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11th December 2011 @ 22:21
SM recovered. === Hydrolysis of PMY 27-1 to give the [url=https://www.chemspider.com/Chemical-Structure.2332829.html]antipyrine glycanamide[/url] for coupling to pyrrole acid core. According to literature reference selective hydrolysis with catalytic base is successful, but not yield given. [b]Reaction Start Time: 09.40 12/12/11[/b] PMY 27-1 (140 mg, 0.38 mmol, 1 equiv.) was stirred in PhMe (20 mL) and heated to reflux. Partial solution. Sodium hydroxide (22 mg, 0.55 mmol, 1.4 equiv.) was added. After 2 hours, TLC shows no reaction. Water (appox. 1 mL) was added. Reaction mixture turns clear then hazy again. After 4 hours (13.40), reaction is a clear solution again. TLC shows conversion to a new product by vanillin dip (overlapping Rf). At 7 hours (16.30), TLC shows SM still remaining. Reaction cooled to room temperature and stored at -20 °C.[i]fumehood shutdown required for 13/12/11[/i]. 0900 15/12/11 Reaction reheated to reflux, still colourless. Still not complete by TLC at 1600 15/12/11. Reaction cooled 0930 16/12/11. TLC shows no change. White crystals form on cooling. Filtered and dried under vacuum (62 mg). 1H NMR consistent with PMY 27-1. Filtrate washed with water (2 × 10 mL), brine, dried (MgSO4) and concentrated to a yellow oil (20 mg). Consistent with SM by 1H NMR. [b]TLC (10% MeOH/DCM) visualised with UV and vanillin:[/b] [data]970[/data][data]972[/data][data]974[/data][data]968[/data] [b]NMR:[/b] [data]1196[/data][data]1194[/data] [b]Reference:[/b] [url=http://jocpr.com/vol2-iss4-2010/JCPR-2-4-410-414.pdf]J. Chem. Pharm. Res., 2010, 2(4):410-41[/url] See also: [blog]1270[/blog] [blog]1224[/blog] [b]Risk and Hazard Assessment:[/b] [data]950[/data]
Attached Files
Risk Assessment
Reaction Scheme
TLC 2 hours
TLC 7 hours
TLC 4 hours, vanillin dip strongly heated
TLC 4 hours, vanillin dip gently heated
1H NMR solid, recov SM
1H NMR oil, recov SM.