Ammonia → N-(3-Mercapto-2-methylpropanoyl)-N-cyclobutylglycine

Participants

Reaction Steps

Ammonia gas was bubbled through a stirred methanolic solution of N-(3-acetylthio-2-methylpropanoyl)-N-cyclobutylglycine (14.1 g, 0.052 mol) for 1 hour. This reaction mixture was left stirring 1 more hour at room temperature. Concentration on a rotary evaporator removed the remaining ammonia and most of the solvent. The residue was rediluted with methanol (500 ml) and the resultant solution was stirred with Bio-Rad AG-50W-X2 cation exchange resin (200 ml) for 1 hour. Filtration followed by concentration of the filtrate yielded 11 g (91%) of a thick yellow oil. This material was purified by HPLC with ethyl acetate, toluene, hexane, acetic acid (25:15:25:1) as the eluent to afford 8.8 g of the compound as a very viscous colorless oil.

Provenance & Evidence