m-Chloroperbenzoic acid → HCID 68545922, compound

Participants

Reaction Steps

Phosphoric acid di-tert-butyl ester 3-{3-fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester was prepared according to the scheme shown in FIG. 16. In a round bottom flask was added 3-{3-Fluoro-4-[6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one (53 mg, 0.1 mmol), Diisopropyl-phosphoramidous acid di-tert-butyl ester (0.078 mL, 0.3 mmol), tetrazole (0.68 mL, ˜0.31 mmol, 0.45 M in MeCN), 15 mL dry THF and 2 mL dry dichloromethane. The resulting reaction mixture was stirred at room temperature for 16 hours before it was then cooled to −78° C. mCPBA (34 mg, 0.15 mmol) was added and the resulting solution was stirred at −78° C. for 2 hours. It was then warmed up to room temperature and diluted with 100 mL EtOAc, washed with saturated aqueous NaHCO3 (2×100 mL), brine, and dried over Na2SO4. Preparative TLC (CH2Cl2/MeOH, v/v, 10:1) gave the titled compound (46 mg, 70% yield) as white solid. ESI MS m/z 664 (M+H). 1H NMR (CDCl3) δ 8.29 (s, 1H), 7.79-7.84 (m, 1H), 7.58 (dd, J=12.8, 2.0 Hz, 1H), 7.45 (s, 1H), 7.39 (t, J=8.8 Hz, 1H), 7.33 (dd, J=8.8, 2.4 Hz, 1H), 6.86 (d, J=8.8 Hz, 1H), 5.77-5.82 (m, 1H), 4.84-4.92 (m, 1H), 4.84 (dd, J=12.4, 2.8 Hz, 1H), 4.55 (dd, J=12.4, 1.6 Hz, 1H), 4.41 (d, J=2.8 Hz, 2H), 4.04-4.27 (m, 4H), 1.49 (s, 9H), 1.45 (s, 9H).

Provenance & Evidence