Lithium hydroxide, monohydrate → HCID 57988322, compound

Participants

Reaction Steps

To a solution of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(butylthio)pyrrolidine-2-carboxylate (135 mg, 0.217 mmol) in THF (1.5 mL) and methanol (1.500 mL) was added pre-made solution of lithium hydroxide monohydrate (18.19 mg, 0.433 mmol) in water (1.5 mL). The resulting cloudy solution was stirred at room for 3 hours. Quenched with 5% citric acid, extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated to afford the desired product (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(butylthio)pyrrolidine-2-carboxylic acid (129 mg, 0.191 mmol, 88% yield) as a white foam. LC-MS (retention time: 3.67 min, method C), MS m/z 609 (M+H).

Provenance & Evidence