Methanol → HCID 69424534, compound

Participants

Reaction Steps

A mixture of (2S,3R)-3-tert-butoxycarbonylamino-2-(2-chloro-acetoxy)-4-(3-fluoro-phenyl)-butyric acid methyl ester (4.56 g, 11.3 mmol, 1 eq), 4N NaOH (6.5 mL, 25.9 mmol, 2.3 eq), MeOH (48 mL) and 1.4-dioxane (72 mL) was stirred at ambient temperature for 4 h after which the solvents were removed in vacuo and the residue was charged with H2O (50 mL) and washed with Et2O (100 mL). The aqueous layer was made acidic with 10% citric acid and extracted with EtOAc (2×75 mL). The combined EtOAc layers were washed with H2O (3×50 mL) brine (50 mL), dried (Na2SO4), concentrated, shaken with heptane and filtered to give the desired acid as a white solid (3.3 g, 94%).

Provenance & Evidence