Lithium hydroxide, monohydrate → HCID 67444162, compound

Participants

Reaction Steps

To a solution of (3S,12R,14S,E)-methyl 12-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-11-thia-1-azabicyclo[10.2.1]pentadec-8-ene-14-carboxylate (90 mg, 0.159 mmol) in THF (1 mL) and MeOH (1.000 mL) was added pre-made solution of lithium hydroxide hydrate (20.06 mg, 0.478 mmol) in Water (1 mL). The resulting cloudy solution was stirred at room for 15 h. LS/MS showed the reaction was only half way done. Another portion of lithium hydroxide hydrate (20.06 mg, 0.478 mmol) was added, and stirred for additional 20 h. Quenched with 5% citric acid, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, evaporated, to afford the desired product (3S,12R,14S,E)-12-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-11-thia-1-azabicyclo[10.2.1]pentadec-8-ene-14-carboxylic acid (72 mg, 0.118 mmol, 73.8% yield) as a white foam. LC-MS (retention time: 3.10 min, method C), MS m/z 551 (M+H).

Provenance & Evidence