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

反応式

[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]

参加物

反応物 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 7361904-Chloro-L-phenylalanine

生成物 1

HCID 27332774-Chloro-DL-phenylalanine methyl ester hydrochloride収率 99%

実験手順

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).