Lithium Hydroxide → HCID 57433086, compound

Participants

Reaction Steps

To a solution of Ethyl (2S,3S,4S)-2-azido-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenylpentanoate (22 mg, 0.058 mmol) in 50% MeOH/THF (800 μL) was added aqueous 1N LiOH (70 μL, 0.070 mmol). The reaction was stirred at rt overnight and concentrated in vacuo. The resulting residue was suspended in EtOAc (30 mL) and washed with aqueous 10% KHSO4 solution (15 ml) and brine (15 mL), and the organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel using an isocratic elution of 10% (10% AcOH/MeOH)/CH2Cl2 and collection and concentration of the appropriate fractions yielded the compound as a yellow residue. 1H NMR (400 MHz, CD3OD) δ 7.23 -7.15 (m, 5H), 4.23-3.87 (m, 3H), 3.21-3.08 (m, 1H), 2.66-2.57 (m, 1H), 1.29 (s, 9H); ES MS (M+23)=373.

Provenance & Evidence