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20th October 2011 @ 01:33
*Wrong user ID used for original post, can no longer edit it Attempts to improve promising results of MW56-3 [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?
Attached Files
MNR11-4 table.PNG
LCMS_mnr11-4.pdf
LCMS_mnr11-5.pdf
LCMS_mnr11-6.pdf
LCMS_mnr11-7.pdf
LCMS_mnr11-8.pdf