Triethylamine → HCID 54046637, compound

Participants

Reaction Steps

A 46 g quantity of S-[(S)-2-benzyloxycarbonylamino-3-phenylpropyl]-L-cysteine ethyl ester and 27 g of 2-bromopropionic acid t-butyl ester were dissolved in 150 ml of HMPA. To the solution was added 18 ml of triethylamine and the mixture was stirred at room temperature for 48 hours. The reaction mixture was poured into ice water and the mixture was extracted with ethyl acetate. The extract was washed with water and with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure and the residue was separated and purified by silica gel column chromatography (a 5:4 mixture of ether and n-hexane as an eluent), giving the α-isomer of the title compound as a colorless oil from the first eluate. Yield 10.6 g.

Provenance & Evidence