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3rd January 2012 @ 04:02
Undesired products formed. === Hydrolysis of PMY 27-1 in aqueous conditions 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: 15.00 03/01/12[/b] PMY 27-1 and recovered SM PMY 28-1-solid (114 mg, 0.38 mmol, 1 equiv.) was stirred in water (20 mL) and sodium hydroxide (2.2 g, 55 mmol, 175 equiv.) was added and the mixture heated to reflux. After 90 minutes, TLC shows reaction complete. Mixture is now a clear, slighly pink, solution. Allowed to cool. 1H NMR not consistent with product. Shows 4-aminoantipyrine. Hydrolysis of the wrong/both amide/s. [b]TLC (10% MeOH/DCM) visualised with UV and vanillin:[/b] [data]990[/data] [b]NMR:[/b] [data]1206[/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]1296[/blog] [blog]1270[/blog] [blog]1224[/blog] [b]Risk and Hazard Assessment:[/b] See: [blog]1296[/blog] [data]950[/data]
Attached Files
TLC 90 minutes
Scheme
1H NMR
Comments
Re: Hydrolysis of benzoyl protected glycinamide PMY 27-1 (PMY 28-2) by OSDD Malaria
25th January 2014 @ 00:06
OSM-S-18 and technically OSM-S-15