Acetic Acid → (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4S)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Step K (1): (3S,5R)-5-((4S,5S)-4-(3,5-difluorobenzyl)-2-oxooxazolidin-5-yl)-1-benzhydrylpyrrolidin-3-yl acetate. To a solution of triphenylphosphine (510 mg, 1.94 mmol) in THF (20 mL) at 0° C. was added DEAD (0.36 mL, 1.94 mmol) and the mixture was allowed to come to rt for 5 min and was again cooled to 0° C. A solution of (4S,5S)-4-(3,5-difluorobenzyl)-5-((2R,4R)-1-benzhydryl-4-hydroxypyrrolidin-2-yl)oxazolidin-2-one (Preparation J, 750 mg, 1.62 mmol) in THF (20 mL) was added and the mixture was allowed to come to rt for 5 min and was again cooled to 0° C. Acetic acid (0.093 mL, 1.62 mmol) was added and the mixture was warmed to rt and stirred for 30 min. pH 7 buffer was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with sat. aqueous NaCl, dried (MgSO4), and concentrated in vacuo. Flash chromatography (silica gel, 5-100% ethyl acetate/hexane) gave 661 mg (81% yield) of the title compound as a clear, very slightly yellow oil: 1H NMR (CDCl3, 500 MHz) δ 1.31-1.34 (1H, m), 2.08-2.16 (1H, m), 2.39 (3H, m), 2.80 (1H, brd s), 3.26 (1H, brd s), 3.60 (2H, brd s), 4.11 (1H, m), 4.27-4.33 (1H, m), 4.91 (2H, m), 5.28 (1H, m), 6.40 (2H, brd s), 6.51 (2H, m), 6.69 (1H, m), 7.22 (1H, m), 7.28-7.49 (8H, m). HPLC retention time: 1.50 min (method A). MS (ESI) (M+H)+ 507.17.

Provenance & Evidence