Citric Acid → HCID 67745436, compound

Participants

Reaction Steps

Diphenylphosphoryl azide (259.2 g), triethylamine (80.8 g) and (S)-2-[1-hydroxy-2-(phenylmethyloxy)ethyl]pyrrolidine (176.6 g) were added to a solution of N-(benzylaminocarbonyl)-L-proline obtained by stirring L-proline (91.9 g), benzyl isocyanate (90.3 g) and triethylamine (80.8 g) in DMF (900 ml) at room temperature for 1 hour, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into a 7% aqueous solution of citric acid and extracted with ethyl acetate. The extract was washed with water, saturated sodium hydrogenbicarbonate and water in order, dried over sodium sulfate, and concentrated to give the title compound (330.9 g).

Provenance & Evidence