Lithium Hydroxide → (2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-3-methyl-4-oxobutanoic acid

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Reaction Steps

To a solution of 4-benzyl 1-methyl N-(tert-butoxycarbonyl)-3-methyl-L-aspartate (Preparation 68, 0.5 g, 1.52 mmol) in THF/water (50 mL/10 mL) was added lithium hydroxide (34 mg, 1.42 mmol) at 0° C. and the reaction stirred warming slowly to room temperature for 18 hours. The reaction was extracted with heptane and the aqueous was acidified with 10% aqueous KHSO4 solution. The solution was extracted with EtOAc, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-60% MeCN in 0.1% formic acid in water to afford the title compound (182 mg, 38%).

Provenance & Evidence