Trifluoroacetic acid → 3-amino-N-(phenylsulfonyl)propanamide
Reaction equation
[O:1]=[C:2]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:3][CH2:4][NH:5]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:5][CH2:4][CH2:3][C:2]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Tert-butyl 3-oxo-3-(phenylsulfonamido)propylcarbamate (3.6 g, 15.1 mmol) was dissolved in dichloromethane (60 mL). Then CF3COOH (1.1 mL, 0.3 mmol, 20 equiv) was added to the mixture at 0° C. and stirred for 2 h at 0° C. The reaction mixture was concentrated and purified by flash chromatograph to give 3-amino-N-(phenylsulfonyl)propanamide as a white solid (1.4 g, 40%). EDI-MS: 229.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ: 7.79˜7.71 (m, 2H), 7.70˜7.43 (brs, 3H), 7.42˜7.34 (m, 3H), 2.83 (t, 2H), 2.24 (t, 2H).