Notice: Undefined index: inline in /home/www/hosts/www.ourexperiment.org/docs/export/xml.php on line 68

Notice: Undefined index: inline in /home/www/hosts/www.ourexperiment.org/docs/export/xml.php on line 68
15551838Preparation of the N-benzoyl-protected 'Ugi-intermediate' (MW51-1)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle high vac) [M.W. 370.4 g/mol] [data=text]779[/data]: strong signal broadening due to rotamers, small impurity -> other NMR solvent, change temperature [data=text]783[/data] Yield after 8 h high vac: 1.25 g (3.36 mmol, 88%) yellow high viscous oil [b]Analytical data:[/b] 1H NMR (CDCl3, 200 MHz, T=328K):[data=text]779[/data]: NMR at higher temperature -> rotamers 1H NMR (CDCl3, 200 MHz, T=328K): δ = 2.85 (t, J=6.9Hz, 2 H), (t, J=6.9Hz, 2 H), 3.47 (d, J=5.0 Hz, 2H), 3.57 (td, J=6.8, J=6.2, 2H), 4.05, (s, 2H), 4.59 (br s, 1H), 6.61 (br s, 1H), 7.19-7.48 (m, 10H). [data=text]935[/data] 1H NMR (CDCl3, 50.3 MHz): δ = 35.5, 40.6, 51.0 (br s), 52.1 (br s), 55.0 (2C), 102.8, 126.5, 126.9 (2C), 128.5 (2C), 128.6 (2C), 128.7 (2C), 130.0, 135.2, 138.8 (br s), 168.8, 173.1. [data=text]783[/data], IR (neat): nu = 2924 cm-1, 3316, 2937, 1623, 1549, 1454, 1239, 1123, 1073, 1024, 976, 698, 551. [data=text]789[/data] MS (ESI, +) m/z (%): 763 [2M + Na]+ (59), 393 [M + Na] (100). HRMS (ESI (+)) Calcd. for [C21H26N2NaO4]+: 393.1785, found: 393.1785. Following reactions: [*] [url=http://www.ourexperiment.org/racemic_pzq/1617]Acid-mediated Pictet-Spengler of the N-benzoyl-Ugi intermediate (MW53-1 to MW53-3)[/url] [*] [url=http://www.ourexperiment.org/racemic_pzq/1654]Synthesis of the N-benzoyl-derivative of PZQ via Pictet-Spengler reaction (MW53-4)[/url] [b]References:[/b] [url=http://v3.espacenet.com/publicationDetails/biblio?CC=WO&NR=2009115333A1&KC=A1&FT=D&date=20090924&DB=EPODOC&locale=en_ep][1] “Novel Synthesis of Praziquantel“, A. Dömling, [i]Patent Application[/i] [b]2009[/b], WO 2009/11533(A1), Language: German.[/url] [url=http://onlinelibrary.wiley.com/doi/10.1002/chem.201002046/abstract][2] "Efficient Multicomponent Reaction Synthesis of the Schistosomiasis Drug Praziquantel", H. Cao, H. Liu, A. Dömling, [i]Chem. Eur. J.[/i] [b]2010[/b], [i]16[/i], (2296 – 12298. DOI: 10.1002/chem.201002046)[/url] [url=http://dx.doi.org/10.1021/jo102058s][3] "Polycyclic Compounds by Ugi−Pictet−Spengler Sequence", W. Wang, S. Ollio, E. Herdtweck, A. Doemling, [i]J. Org. Chem.[/i] [b]2011[/b], [i]76[/i] 2, 637–644. (DOI: 10.1021/jo102058)[/url]]]>N-benzoyl derivative of the 'Ugi-intermediate' (MW36) via Ugi reaction

Reaction Scheme correction


See also:
  • Optimizing conditions for the Ugi reaction (MW36-2 to MW36-5)
  • Preparation of the dimethoxy ‘Ugi-intermediate’ via Ugi reaction (MW40)
  • N-Cyclohexanoyl-protection of the amine intermediate MW7-2-27 of PZQ (MW29-1 to MW29-3) (alternative approach to the Ugi-intermediate via Shin Poong route)


    Hazard and Risk Assessment:
  • HRAF MW51.pdf


    Start time: 5:10 PM 8/02/2011
    End time: 7:00 PM 9/02/2011

    To a mixture of paraformaldehyde (114 mg, 3.81 mmol, 1.0 eq.), 2,2-dimethoxyethylamine (aminoacetaldehyde dimethyl acetal (401 mg, 3.81 mmol, 412 µL, 1.0 eq., M.W. 105.1 g/mol, d=0.973 g/mL) and benzoic acid (465 mg, 3.81 mmol, 1.0 eq., M.W. 122.12 g/mol) in methanol (2 mL) was added slowly 2-phenylethyl isocyanide (MW34-1) (500 mg, 3.81 mmol, 1.0 eq., M.W. 131.2, d=0.95 g/mL) and stirred at room temperature for 26 h.

    Note: 2-phenylethyl isocyanide was purified before use by flush chromatography (silica gel, hexane:ethyl acetate = 4:1), because the pale brown oil became a dark brown gel while stored in the fridge for 6 month.
    - solvent evaporated
    - column chromatography (silica gel, ethyl acetate 100%)

    Yield: 1.37 g (3.69 mmol, 97%) yellow oil (solvent impurities -> high vac)
    [M.W. 370.4 g/mol]
    Data: 1H NMR MW51-1.pdf: strong signal broadening due to rotamers, small impurity
    -> other NMR solvent, change temperature
    Data: 13C NMR MW51-1.pdf

    Yield after 8 h high vac: 1.25 g (3.36 mmol, 88%) yellow high viscous oil

    Analytical data:
    1H NMR (CDCl3, 200 MHz, T=328K):Data: 1H NMR MW51-1.pdf: NMR at higher temperature -> rotamers
    1H NMR (CDCl3, 200 MHz, T=328K): δ = 2.85 (t, J=6.9Hz, 2 H), (t, J=6.9Hz, 2 H), 3.47 (d, J=5.0 Hz, 2H), 3.57 (td, J=6.8, J=6.2, 2H), 4.05, (s, 2H), 4.59 (br s, 1H), 6.61 (br s, 1H), 7.19-7.48 (m, 10H). Data: 1H NMR MW51-1 T=328K.pdf
    1H NMR (CDCl3, 50.3 MHz): δ = 35.5, 40.6, 51.0 (br s), 52.1 (br s), 55.0 (2C), 102.8, 126.5, 126.9 (2C), 128.5 (2C), 128.6 (2C), 128.7 (2C), 130.0, 135.2, 138.8 (br s), 168.8, 173.1. Data: 13C NMR MW51-1.pdf,
    IR (neat): nu = 2924 cm-1, 3316, 2937, 1623, 1549, 1454, 1239, 1123, 1073, 1024, 976, 698, 551. Data: IR MW51-1.pdf
    MS (ESI, +) m/z (%): 763 [2M + Na]+ (59), 393 [M + Na] (100).
    HRMS (ESI (+)) Calcd. for [C21H26N2NaO4]+: 393.1785, found: 393.1785.


    Following reactions:
  • Acid-mediated Pictet-Spengler of the N-benzoyl-Ugi intermediate (MW53-1 to MW53-3)
  • Synthesis of the N-benzoyl-derivative of PZQ via Pictet-Spengler reaction (MW53-4)


    References:
  • [1] “Novel Synthesis of Praziquantel“, A. Dömling, Patent Application 2009, WO 2009/11533(A1), Language: German.

    [2] "Efficient Multicomponent Reaction Synthesis of the Schistosomiasis Drug Praziquantel", H. Cao, H. Liu, A. Dömling, Chem. Eur. J. 2010, 16, (2296 – 12298. DOI: 10.1002/chem.201002046)

    [3] "Polycyclic Compounds by Ugi−Pictet−Spengler Sequence", W. Wang, S. Ollio, E. Herdtweck, A. Doemling, J. Org. Chem. 2011, 76 2, 637–644. (DOI: 10.1021/jo102058)
    Linked Posts
    ]]>2011-02-07T07:56:59+00:002011-03-21T08:22:45+00:0065cde40c5c9570298815f56125dcf798dhttps://www.ourexperiment.org/data/765.xmlhttps://www.ourexperiment.org/data/767.xmlhttps://www.ourexperiment.org/data/769.xmlhttps://www.ourexperiment.org/data/779.xmlhttps://www.ourexperiment.org/data/781.xmlhttps://www.ourexperiment.org/data/783.xmlhttps://www.ourexperiment.org/data/789.xmlhttps://www.ourexperiment.org/data/935.xmlhttps://www.ourexperiment.org/data/937.xmlhttps://www.ourexperiment.org/data/955.xmlhttps://www.ourexperiment.org/data/957.xmlhttp://www.ourexperiment.org/uri/102https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.htmlhttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.htmlhttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xmlhttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.pnghttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1555https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1556https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1557https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1558https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1559https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1560https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1561https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1562https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1571https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1572https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1576https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1580https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1581https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1582https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1583https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1584https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1591https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1592https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1593https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1605https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1809https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1810https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1811https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1812https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1813https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1821https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1836https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1837https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1838https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=7072
    15557072Preparation of the N-benzoyl-protected 'Ugi-intermediate' (MW51-1)
    Experiments
    profiles.google.com-micha.wolfleMichael Wolfle high vac) [M.W. 370.4 g/mol] [data=text]779[/data]: strong signal broadening due to rotamers, small impurity -> other NMR solvent, change temperature [data=text]783[/data] Yield after 8 h high vac: 1.25 g (3.36 mmol, 88%) yellow high viscous oil [b]Analytical data:[/b] 1H NMR (CDCl3, 200 MHz, T=328K):[data=text]779[/data]: NMR at higher temperature -> rotamers 1H NMR (CDCl3, 200 MHz, T=328K): δ = 2.85 (t, J=6.9Hz, 2 H), (t, J=6.9Hz, 2 H), 3.47 (d, J=5.0 Hz, 2H), 3.57 (td, J=6.8, J=6.2, 2H), 4.05, (s, 2H), 4.59 (br s, 1H), 6.61 (br s, 1H), 7.19-7.48 (m, 10H). [data=text]935[/data] 1H NMR (CDCl3, 50.3 MHz): δ = 35.5, 40.6, 51.0 (br s), 52.1 (br s), 55.0 (2C), 102.8, 126.5, 126.9 (2C), 128.5 (2C), 128.6 (2C), 128.7 (2C), 130.0, 135.2, 138.8 (br s), 168.8, 173.1. [data=text]783[/data], IR (neat): nu = 2924 cm-1, 3316, 2937, 1623, 1549, 1454, 1239, 1123, 1073, 1024, 976, 698, 551. [data=text]789[/data] MS (ESI, +) m/z (%): 763 [2M + Na]+ (59), 393 [M + Na] (100). HRMS (ESI (+)) Calcd. for [C21H26N2NaO4]+: 393.1785, found: 393.1785. Following reactions: [*] [url=http://www.ourexperiment.org/racemic_pzq/1617]Acid-mediated Pictet-Spengler of the N-benzoyl-Ugi intermediate (MW53-1 to MW53-3)[/url] [*] [url=http://www.ourexperiment.org/racemic_pzq/1654]Synthesis of the N-benzoyl-derivative of PZQ via Pictet-Spengler reaction (MW53-4)[/url] [b]References:[/b] [url=http://v3.espacenet.com/publicationDetails/biblio?CC=WO&NR=2009115333A1&KC=A1&FT=D&date=20090924&DB=EPODOC&locale=en_ep][1] “Novel Synthesis of Praziquantel“, A. Dömling, [i]Patent Application[/i] [b]2009[/b], WO 2009/11533(A1), Language: German.[/url] [url=http://onlinelibrary.wiley.com/doi/10.1002/chem.201002046/abstract][2] "Efficient Multicomponent Reaction Synthesis of the Schistosomiasis Drug Praziquantel", H. Cao, H. Liu, A. Dömling, [i]Chem. Eur. J.[/i] [b]2010[/b], [i]16[/i], (2296 – 12298. DOI: 10.1002/chem.201002046)[/url] [url=http://dx.doi.org/10.1021/jo102058s][3] "Polycyclic Compounds by Ugi−Pictet−Spengler Sequence", W. Wang, S. Ollio, E. Herdtweck, A. Doemling, [i]J. Org. Chem.[/i] [b]2011[/b], [i]76[/i] 2, 637–644. (DOI: 10.1021/jo102058)[/url]]]>N-benzoyl derivative of the 'Ugi-intermediate' (MW36) via Ugi reaction

    Reaction Scheme correction


    See also:
  • Optimizing conditions for the Ugi reaction (MW36-2 to MW36-5)
  • Preparation of the dimethoxy ‘Ugi-intermediate’ via Ugi reaction (MW40)
  • N-Cyclohexanoyl-protection of the amine intermediate MW7-2-27 of PZQ (MW29-1 to MW29-3) (alternative approach to the Ugi-intermediate via Shin Poong route)


    Hazard and Risk Assessment:
  • HRAF MW51.pdf


    Start time: 5:10 PM 8/02/2011
    End time: 7:00 PM 9/02/2011

    To a mixture of paraformaldehyde (114 mg, 3.81 mmol, 1.0 eq.), 2,2-dimethoxyethylamine (aminoacetaldehyde dimethyl acetal (401 mg, 3.81 mmol, 412 µL, 1.0 eq., M.W. 105.1 g/mol, d=0.973 g/mL) and benzoic acid (465 mg, 3.81 mmol, 1.0 eq., M.W. 122.12 g/mol) in methanol (2 mL) was added slowly 2-phenylethyl isocyanide (MW34-1) (500 mg, 3.81 mmol, 1.0 eq., M.W. 131.2, d=0.95 g/mL) and stirred at room temperature for 26 h.

    Note: 2-phenylethyl isocyanide was purified before use by flush chromatography (silica gel, hexane:ethyl acetate = 4:1), because the pale brown oil became a dark brown gel while stored in the fridge for 6 month.
    - solvent evaporated
    - column chromatography (silica gel, ethyl acetate 100%)

    Yield: 1.37 g (3.69 mmol, 97%) yellow oil (solvent impurities -> high vac)
    [M.W. 370.4 g/mol]
    Data: 1H NMR MW51-1.pdf: strong signal broadening due to rotamers, small impurity
    -> other NMR solvent, change temperature
    Data: 13C NMR MW51-1.pdf

    Yield after 8 h high vac: 1.25 g (3.36 mmol, 88%) yellow high viscous oil

    Analytical data:
    1H NMR (CDCl3, 200 MHz, T=328K):Data: 1H NMR MW51-1.pdf: NMR at higher temperature -> rotamers
    1H NMR (CDCl3, 200 MHz, T=328K): δ = 2.85 (t, J=6.9Hz, 2 H), (t, J=6.9Hz, 2 H), 3.47 (d, J=5.0 Hz, 2H), 3.57 (td, J=6.8, J=6.2, 2H), 4.05, (s, 2H), 4.59 (br s, 1H), 6.61 (br s, 1H), 7.19-7.48 (m, 10H). Data: 1H NMR MW51-1 T=328K.pdf
    1H NMR (CDCl3, 50.3 MHz): δ = 35.5, 40.6, 51.0 (br s), 52.1 (br s), 55.0 (2C), 102.8, 126.5, 126.9 (2C), 128.5 (2C), 128.6 (2C), 128.7 (2C), 130.0, 135.2, 138.8 (br s), 168.8, 173.1. Data: 13C NMR MW51-1.pdf,
    IR (neat): nu = 2924 cm-1, 3316, 2937, 1623, 1549, 1454, 1239, 1123, 1073, 1024, 976, 698, 551. Data: IR MW51-1.pdf
    MS (ESI, +) m/z (%): 763 [2M + Na]+ (59), 393 [M + Na] (100).
    HRMS (ESI (+)) Calcd. for [C21H26N2NaO4]+: 393.1785, found: 393.1785.


    Following reactions:
  • Acid-mediated Pictet-Spengler of the N-benzoyl-Ugi intermediate (MW53-1 to MW53-3)
  • Synthesis of the N-benzoyl-derivative of PZQ via Pictet-Spengler reaction (MW53-4)


    References:
  • [1] “Novel Synthesis of Praziquantel“, A. Dömling, Patent Application 2009, WO 2009/11533(A1), Language: German.

    [2] "Efficient Multicomponent Reaction Synthesis of the Schistosomiasis Drug Praziquantel", H. Cao, H. Liu, A. Dömling, Chem. Eur. J. 2010, 16, (2296 – 12298. DOI: 10.1002/chem.201002046)

    [3] "Polycyclic Compounds by Ugi−Pictet−Spengler Sequence", W. Wang, S. Ollio, E. Herdtweck, A. Doemling, J. Org. Chem. 2011, 76 2, 637–644. (DOI: 10.1021/jo102058)
    Linked Entries
    ]]>2011-02-07T07:56:59+00:002015-05-30T22:29:40+01:006https://www.ourexperiment.org/data/765.xmlhttps://www.ourexperiment.org/data/767.xmlhttps://www.ourexperiment.org/data/769.xmlhttps://www.ourexperiment.org/data/779.xmlhttps://www.ourexperiment.org/data/781.xmlhttps://www.ourexperiment.org/data/783.xmlhttps://www.ourexperiment.org/data/789.xmlhttps://www.ourexperiment.org/data/935.xmlhttps://www.ourexperiment.org/data/937.xmlhttps://www.ourexperiment.org/data/955.xmlhttps://www.ourexperiment.org/data/957.xmlhttp://www.ourexperiment.org/uri/102https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.htmlhttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.htmlhttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xmlhttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.pnghttps://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1555https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1556https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1557https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1558https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1559https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1560https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1561https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1562https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1571https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1572https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1576https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1580https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1581https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1582https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1583https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1584https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1591https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1592https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1593https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1605https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1809https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1810https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1811https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1812https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1813https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1821https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1836https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1837https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=1838https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=7072https://www.ourexperiment.org/racemic_pzq/1555/Preparation_of_the_Nbenzoylprotected_Ugiintermediate_MW511.xml?revision=-1