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25246074Continuation of Acid-catalyzed Pictet-Spengler 0f MNR8-2 using binaphthalenedisulfonic acid to give MNR11
Experiments
plus.google.com-113014781212630252105Murray Robertson [b]Hazard and Risk Assessment:[/b] As for [url=http://www.ourexperiment.org/racemic_pzq/2420/Acidmediated_PictetSpengler_of_MNR82_to_give_dimethoxy_PZQ_analog_MNR113.html]MNR11-3[/url] [b]Procedure[/b] [b]MNR11-4[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was heated at reflux overnight [b]MNR11-5[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was heated at reflux overnight [b]MNR11-6[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was stirred at room temperature overnight [b]MNR11-7[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was stirred at room temperature overnight [b]MNR11-8[/b] MNR8-2(100 mg, 0.22 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (20 mg, 0.02 mmol) toluene (2 mL) was stirred at room temperature overnight TLC of all 5 reactions after 16 hours showed very little reaction. MNR11-5 (refluxing chloroform) showed signs of possible product. After 20 hours a sample of MNR11-5 was removed from the reaction and filtered through a pipette of silica and ran through the LCMS. All 5 reactions were left at their original temperatures for 44 hours then at room temperature over the weekend. After 2.5 days at room temperature a small aliquot from each reaction was removed and filtered through a small silca column (pipette) and submitted for LCMS [b]MNR11-4[/b] [url=http://www.ourexperiment.org/data/files/1491/LCMS_mnr11-4.pdf]LCMS MNR11-4[/url] Ret. Time 16.100 373.2 [M+H] 20.167 487.3 [SM+Na] *Showing signs of cyclisation [b]MNR11-5[/b] [url=http://www.ourexperiment.org/data/files/1493/LCMS_mnr11-5.pdf]LCMS MNR11-5[/url] Ret. Time 16.192 373.2 [M+H] 20.658 487.3 [SM+Na] More significant peak for unwanted hemiaminal at 19.167 [b]MNR11-6[/b] [url=http://www.ourexperiment.org/data/files/1495/LCMS_mnr11-6.pdf]LCMS MNR11-6[/url] Ret. Time 16.183 373.2 [M+H] 19.983 487.3 [SM+Na] 419.3 [Hemiaminal+H] 20.5 481.1 Unknown 21.025 556 Unknown No peak at 19.1 (good) but side reactions going on (?) [b]MNR11-7[/b] [url=http://www.ourexperiment.org/data/files/1497/LCMS_mnr11-7.pdf]LCMS MNR11-7[/url] Ret. Time 14.167 373.2 [M+H] 19.217 487.3 [SM+Na] 419.3 [Hemiaminal+H] Mainly starting material. [b]MNR11-8[/b] [url=http://www.ourexperiment.org/data/files/1499/LCMS_mnr11-8.pdf]LCMS MNR11-8[/url] Ret. Time 16.067 373.2 [M+H] 19.917 487.3 [SM+Na] 419.3 [Hemiaminal+H] 20.442 481.1 Unknown 21.025 556 Unknown No peak at 19.1 (good) but side reactions going on (?) Next step: Repeat DCM at reflux and try toluene at reflux for longer reaction time?]]>
Attempts to improve promising results of MW56-3





Hazard and Risk Assessment:
As for MNR11-3

Procedure

MNR11-4
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was heated at reflux overnight

MNR11-5
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was heated at reflux overnight

MNR11-6
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was stirred at room temperature overnight

MNR11-7
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was stirred at room temperature overnight

MNR11-8
MNR8-2(100 mg, 0.22 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (20 mg, 0.02 mmol) toluene (2 mL) was stirred at room temperature overnight

TLC of all 5 reactions after 16 hours showed very little reaction. MNR11-5 (refluxing chloroform) showed signs of possible product. After 20 hours a sample of MNR11-5 was removed from the reaction and filtered through a pipette of silica and ran through the LCMS.

All 5 reactions were left at their original temperatures for 44 hours then at room temperature over the weekend.

After 2.5 days at room temperature a small aliquot from each reaction was removed and filtered through a small silca column (pipette) and submitted for LCMS

MNR11-4

LCMS MNR11-4
Ret. Time 16.100 373.2 [M+H]
20.167 487.3 [SM+Na]

*Showing signs of cyclisation


MNR11-5

LCMS MNR11-5

Ret. Time 16.192 373.2 [M+H]
20.658 487.3 [SM+Na]


More significant peak for unwanted hemiaminal at 19.167

MNR11-6

LCMS MNR11-6
Ret. Time 16.183 373.2 [M+H]
19.983 487.3 [SM+Na]
419.3 [Hemiaminal+H]
20.5 481.1 Unknown
21.025 556 Unknown

No peak at 19.1 (good) but side reactions going on (?)

MNR11-7

LCMS MNR11-7
Ret. Time 14.167 373.2 [M+H]
19.217 487.3 [SM+Na]
419.3 [Hemiaminal+H]

Mainly starting material.

MNR11-8

LCMS MNR11-8
Ret. Time 16.067 373.2 [M+H]
19.917 487.3 [SM+Na]
419.3 [Hemiaminal+H]
20.442 481.1 Unknown
21.025 556 Unknown
No peak at 19.1 (good) but side reactions going on (?)

Next step: Repeat DCM at reflux and try toluene at reflux for longer reaction time?
Linked Posts
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]]>2011-10-20T01:33:05+01:002012-07-12T00:21:09+01:00672b4ce75d4406d11e4b297e3d2ebdfcchttps://www.ourexperiment.org/data/1490.xmlhttps://www.ourexperiment.org/data/1492.xmlhttps://www.ourexperiment.org/data/1494.xmlhttps://www.ourexperiment.org/data/1496.xmlhttps://www.ourexperiment.org/data/1498.xmlhttps://www.ourexperiment.org/data/1500.xmlhttp://www.ourexperiment.org/uri/18bhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.htmlhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.htmlhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xmlhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.pnghttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2524https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2525https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2526https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2527https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2528https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2529https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2530https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2531https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2532https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2533https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2536https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=6074https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=7264
25247264Continuation of Acid-catalyzed Pictet-Spengler 0f MNR8-2 using binaphthalenedisulfonic acid to give MNR11
Experiments
plus.google.com-113014781212630252105Murray Robertson [b]Hazard and Risk Assessment:[/b] As for [url=http://www.ourexperiment.org/racemic_pzq/2420/Acidmediated_PictetSpengler_of_MNR82_to_give_dimethoxy_PZQ_analog_MNR113.html]MNR11-3[/url] [b]Procedure[/b] [b]MNR11-4[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was heated at reflux overnight [b]MNR11-5[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was heated at reflux overnight [b]MNR11-6[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was stirred at room temperature overnight [b]MNR11-7[/b] MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was stirred at room temperature overnight [b]MNR11-8[/b] MNR8-2(100 mg, 0.22 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (20 mg, 0.02 mmol) toluene (2 mL) was stirred at room temperature overnight TLC of all 5 reactions after 16 hours showed very little reaction. MNR11-5 (refluxing chloroform) showed signs of possible product. After 20 hours a sample of MNR11-5 was removed from the reaction and filtered through a pipette of silica and ran through the LCMS. All 5 reactions were left at their original temperatures for 44 hours then at room temperature over the weekend. After 2.5 days at room temperature a small aliquot from each reaction was removed and filtered through a small silca column (pipette) and submitted for LCMS [b]MNR11-4[/b] [url=http://www.ourexperiment.org/data/files/1491/LCMS_mnr11-4.pdf]LCMS MNR11-4[/url] Ret. Time 16.100 373.2 [M+H] 20.167 487.3 [SM+Na] *Showing signs of cyclisation [b]MNR11-5[/b] [url=http://www.ourexperiment.org/data/files/1493/LCMS_mnr11-5.pdf]LCMS MNR11-5[/url] Ret. Time 16.192 373.2 [M+H] 20.658 487.3 [SM+Na] More significant peak for unwanted hemiaminal at 19.167 [b]MNR11-6[/b] [url=http://www.ourexperiment.org/data/files/1495/LCMS_mnr11-6.pdf]LCMS MNR11-6[/url] Ret. Time 16.183 373.2 [M+H] 19.983 487.3 [SM+Na] 419.3 [Hemiaminal+H] 20.5 481.1 Unknown 21.025 556 Unknown No peak at 19.1 (good) but side reactions going on (?) [b]MNR11-7[/b] [url=http://www.ourexperiment.org/data/files/1497/LCMS_mnr11-7.pdf]LCMS MNR11-7[/url] Ret. Time 14.167 373.2 [M+H] 19.217 487.3 [SM+Na] 419.3 [Hemiaminal+H] Mainly starting material. [b]MNR11-8[/b] [url=http://www.ourexperiment.org/data/files/1499/LCMS_mnr11-8.pdf]LCMS MNR11-8[/url] Ret. Time 16.067 373.2 [M+H] 19.917 487.3 [SM+Na] 419.3 [Hemiaminal+H] 20.442 481.1 Unknown 21.025 556 Unknown No peak at 19.1 (good) but side reactions going on (?) Next step: Repeat DCM at reflux and try toluene at reflux for longer reaction time?]]>
Attempts to improve promising results of MW56-3





Hazard and Risk Assessment:
As for MNR11-3

Procedure

MNR11-4
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was heated at reflux overnight

MNR11-5
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was heated at reflux overnight

MNR11-6
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) DCM (1 mL) was stirred at room temperature overnight

MNR11-7
MNR8-2(50 mg, 0.11 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (10 mg, 0.01 mmol) chloroform (1 mL) was stirred at room temperature overnight

MNR11-8
MNR8-2(100 mg, 0.22 mmol) and 1,1’-Binaphthalene-2,2’-disulfonic acid, MW54-3 (20 mg, 0.02 mmol) toluene (2 mL) was stirred at room temperature overnight

TLC of all 5 reactions after 16 hours showed very little reaction. MNR11-5 (refluxing chloroform) showed signs of possible product. After 20 hours a sample of MNR11-5 was removed from the reaction and filtered through a pipette of silica and ran through the LCMS.

All 5 reactions were left at their original temperatures for 44 hours then at room temperature over the weekend.

After 2.5 days at room temperature a small aliquot from each reaction was removed and filtered through a small silca column (pipette) and submitted for LCMS

MNR11-4

LCMS MNR11-4
Ret. Time 16.100 373.2 [M+H]
20.167 487.3 [SM+Na]

*Showing signs of cyclisation


MNR11-5

LCMS MNR11-5

Ret. Time 16.192 373.2 [M+H]
20.658 487.3 [SM+Na]


More significant peak for unwanted hemiaminal at 19.167

MNR11-6

LCMS MNR11-6
Ret. Time 16.183 373.2 [M+H]
19.983 487.3 [SM+Na]
419.3 [Hemiaminal+H]
20.5 481.1 Unknown
21.025 556 Unknown

No peak at 19.1 (good) but side reactions going on (?)

MNR11-7

LCMS MNR11-7
Ret. Time 14.167 373.2 [M+H]
19.217 487.3 [SM+Na]
419.3 [Hemiaminal+H]

Mainly starting material.

MNR11-8

LCMS MNR11-8
Ret. Time 16.067 373.2 [M+H]
19.917 487.3 [SM+Na]
419.3 [Hemiaminal+H]
20.442 481.1 Unknown
21.025 556 Unknown
No peak at 19.1 (good) but side reactions going on (?)

Next step: Repeat DCM at reflux and try toluene at reflux for longer reaction time?
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]]>2011-10-20T01:33:05+01:002015-08-13T15:59:13+01:006https://www.ourexperiment.org/data/1490.xmlhttps://www.ourexperiment.org/data/1492.xmlhttps://www.ourexperiment.org/data/1494.xmlhttps://www.ourexperiment.org/data/1496.xmlhttps://www.ourexperiment.org/data/1498.xmlhttps://www.ourexperiment.org/data/1500.xmlhttp://www.ourexperiment.org/uri/18bhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.htmlhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.htmlhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xmlhttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.pnghttps://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2524https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2525https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2526https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2527https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2528https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2529https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2530https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2531https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2532https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2533https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=2536https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=6074https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=7264https://www.ourexperiment.org/racemic_pzq/2524/Continuation_of_Acidcatalyzed_PictetSpengler_0f_MNR82_using_binaphthalenedisulfonic_acid_to_give_MNR11.xml?revision=-1