Phenyl chloroformate → Phenyl 4-(1,2,3-trihydroxypropan-2-yl)phenylcarbamate

反応式

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:13])([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C1COCC1.O>[OH:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:6]=1)([OH:13])[CH2:11][OH:12]

参加物

実験手順

To a stirred solution of 2-(4-aminophenyl)propane-1,2,3-triol (900 mg, 4.918 mmol, 1.0 eq) in THF/H2O/sat. NaHCO3 (4 mL: 2 mL: 4 mL) was added phenyl chloroformate (0.68 mL, 5.367 mmol, 1.1 eq) at 0° C. and the mixture was stirred at RT for 0.5 h, then the THF was evaporated, the residue was diluted with EtOAc (20 mL), washed with water (20 mL) followed by brine and the solvent evaporated. The resulting residue was purified by CC using MeOH/CHCl3 (1:19) as eluent to get phenyl 4-(1,2,3-trihydroxypropan-2-yl)phenylcarbamate (900 mg, 60%, white solid; TLC system: MeOH/CHCl3 (1:9), Rf: 0.4).