Isobutyl chloroformate → HCID 86596238, compound
Reaction equation
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])=[O:5].Cl[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18]>CC(N(C)C)=O>[CH2:20]([O:19][C:17]([S:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])=[O:5])=[O:18])[CH:21]([CH3:23])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-(2-mercaptobenzoyl)-L-alaninamide (0.22 g, 1.00 mmol) in DMA (5 ml) was added iso-butyl chloroformate (0.2 g, 1.50 mmol), and the mixture was stirred for 8 h. The solvent was evaporated to dryness, and the residue was triturated with ethyl ether (25 ml). The precipitate obtained was filtered, washed with water and dried over CaCl2. Yield, 73%. The product was further purified by column chromatography on silica using chloroform-methanol (7:3 v/v) as eluent with 82% recovery. 1H NMR (DMSO-d6): 0.94(d, 6H, 2CH3), 1.34(d, 3H, CH3), 1.96(m, 1H, CH), 4.06(d, 2H, CH2), 4.44quintet, 1H, CH), 7.16(brs, 1H, NH2), 7.38(brs, 1H, NH2), 7.54-7.80(m, 4H, Ar—H), 8.42(d, 1H, NH).