Sodium borohydride → N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester

Participants

Reaction Steps

A solution of N-[(carbobenzyloxycarbonyl)valinyl]-3-amino-4-oxo-5-(2,3,5,6-tetrafluorophenyloxy)-pentanoic acid, tert-butyl ester (6.18 g, 10.57 mmol) in 1:1 MeOH/THF (100 ml) was cooled to 0° C. and NaBH4 (1.20 g, 31.72 mmol) was added and stirred for 2 hours. The reaction was diluted with saturated NH4Cl and extracted with CH2Cl2 (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the titled product as a white solid (6.14 g, 10.46 mmol, 98%). MS C28H34N2O7, [M+Na]+ =609, [M−H]−=585.

Provenance & Evidence