Diisopropylethylamine → HCID 68802560, compound

Participants

Reaction Steps

To a solution of (S)-phenylalanine ethyl ester hydrochloride (5.09 g, 22.2 mmol) and tert-butyloxycarbonylphenylglycine (5.06 g, 20.1 mmol) in N,N-dimethylformamide (100 mL) was added diisopropylethylamine (4.2 mL, 24.1 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexaflurorophosphate (9.16 g, 24.2 mmol) and the mixture stirred at ambient temperature overnight. The reaction mixture was poured into ethyl acetate (750 mL), washed with 1:1 1M aqueous hydrochloric acid/brine (2×75 mL), 1:1 saturated aqueous sodium bicarbonate solution/brine (2×75 mL), brine (200 mL), dried over sodium sulfate and concentrated in vacuo to give 2-(S)-(2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-phenyl-propionic acid ethyl ester as a pale yellow solid which still contained some N,N-dimethylformamide.

Provenance & Evidence