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23rd April 2013 @ 01:07
Mnr: 11-20
As for
Synthesis of MNR11-17
and
Synthesis of MNR11-16

Starting material from
Preparation of the dimethoxy Ugi-intermediate (MNR8-5)

MNR11-18%20scheme.png

MNR11-18%20table.PNG

Hazard and Risk Assessment:
HIRAC MNR11.pdf


Procedure:
To a solution of MNR8-5 (4.88 g, 10.5 mmol) in toluene (35 mL) at room temperature was added methanesulfonic acid (1.47 mL, 22.58 mmol) and the mixture was refluxed for 1 hour. The reaction was allowed to cool to room temperature and was quenched with saturated sodium carbonate and extracted with EtOAc (50 mL x 3). The organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude as a thick orange oil.

Crude - 3.965 g, 101 %

TLC
100% EtOAc. Starting material, co=spot, reaction mixture after work up
2013-04-22 16.41.25.jpg


NMR
mnr11-18_crude_vs_mnr11-17.pdf
mnr11-18_crude_1H.pdf
mnr11-18_crude.zip


Conclusion
Crude product taken on to the next step without further purification.

Hydrolysis of MNR11-18 to give MNR26-7

Strings
Starting material
InChI=1S/C25H40N2O6/c1-5-32-24(33-6-2)18-27(25(29)20-10-8-7-9-11-20)17-23(28)26-15-14-19-12-13-21(30-3)22(16-19)31-4/h12-13,16,20,24H,5-11,14-15,17-18H2,1-4H3,(H,26,28)
Product
InChI=1S/C21H28N2O4/c1-26-18-10-15-8-9-23-17(16(15)11-19(18)27-2)12-22(13-20(23)24)21(25)14-6-4-3-5-7-14/h10-11,14,17H,3-9,12-13H2,1-2H3
Linked Entries
Attached Files
MNR11-18 scheme.png
MNR11-18 table.PNG
mnr11-18_crude_vs_mnr11-17.pdf
mnr11-18_crude_1H.pdf
mnr11-18_crude.zip
2013-04-22 16.41.25.jpg