Methanol → 4-Chloro-DL-phenylalanine methyl ester hydrochloride

반응식

[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:18]O>>[ClH:1].[NH2:8][CH:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:13][CH:12]=1)[C:9]([O:11][CH3:18])=[O:10]

참가 물질

반응물 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 7361904-Chloro-L-phenylalanine

생성물 1

HCID 27332774-Chloro-DL-phenylalanine methyl ester hydrochloride수율 99%

실험 절차

While under nitrogen, a stirred suspension of 4-chlorophenylalanine (2.50 g, 12.5 mmol) in anhydrous methanol (18 mL) was cooled in an ice-water bath and carefully treated with thionyl chloride (1.00 mL, 13.8 mmol). After stirring for 10 min, and the cooling bath was removed and the mixture was allowed to warm to room temperature. A reflux condenser was attached, and the slurry was warmed to 55° C. After stirring overnight, the mixture was cooled to room temperature, concentrated and dried under reduced pressure to give methyl 2-amino-3-(4-chlorophenyl)propanoate hydrochloride (3.13 g, 99%) as a white solid. ESI+ MS found for C10H12ClNO2 m/z 214.0 (M+H).