Lithium Hydroxide → HCID 59746631, compound

Participants

Reaction Steps

To a solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((R)-2-(4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)oxazolidin-2-one (Step A (8), 420 mg, 0.9 mmol) in EtOH (20 mL) was added a solution of LiOH (217 mg, 9 mmol) in H2O (5 mL). This reaction mixture was brought to 60° C. and stirred overnight. The mixture was then concentrated in vacuo. Ethyl ether (100 mL) was added to the mixture and washed with 1N HCl (80 mL) twice. The aqueous phase was basified to pH 12 with 50% aqueous NaOH solution. This mixture was extracted with ethyl acetate (100 mL) twice. The combined organic layer was dried (Na2SO4), and concentrated in vacuo to give 345 mg of the title compound of Preparation A: 1H NMR (CDCl3, 500 MHz) δ 1.78 (2H, brd s), 2.44 (1H, dd, J=10, 15 Hz), 2.93 (1H, m), 3.01-3.07 (3H, m), 3.36 (1H, s), 3.60-3.69 (3H, m), 3.80 (3H, s), 6.69 (1H, m), 6.77-6.81 (2H, m), 6.86 (2H, d, J=10 Hz), 6.98 (1H, d, J=5 Hz), 7.12-7.18 (3H, m), 7.24 (2H, d, J=10 Hz). MS (ESI)(M+H)+ 439.12.

Provenance & Evidence