Triethylamine → HCID 66940370, compound

Reaction equation

[CH3:1][S:2][CH2:3][CH2:4][C:5](Cl)=[O:6].Cl.[CH3:9][O:10][C:11](=[O:21])[C@H:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:13].C(N(CC)CC)C>ClCCl>[CH3:9][O:10][C:11](=[O:21])[CH:12]([NH:13][C:5](=[O:6])[CH2:4][CH2:3][S:2][CH3:1])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Procedure

1.556 g (11 mmol) of 3-methylsulfanyl-propionyl chloride was added slowly to a mixture of 2.20 g (10 mmol) of phenylalanine methyl ester hydrochloride, 4.18 mL (30 mmol) of triethyl amine and 50 mL of dichloromethane and stirred at room temperature for 2 h. The reaction mixture was partitioned between DCM (50 mL) and saturated NaHCO3 solution (100 mL). The aqueous layer was separated and extracted again with dichloromethane (100 mL). The combined organic extracts were dried over sodium sulfate and evaporated. Purification by column chromatography on silica gel gave 2.574 g (92%) of 2-(3-methylsulfanyl-propionylamino)-3-phenyl-propionic acid methyl ester. LCMS: 282 (M+1)+.