Boron tribromide → HCID 59485723, compound

Participants

Reaction Conditions

Reaction Steps

To a 10 mL round bottom flask is charged with (4S,5S)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-5-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)oxazolidin-2-one (264 mg, 0.57 mmol) and DCM (6 mL) and is cooled to −78° C. Boron tribromide (1M, 2.3 mL, 2.3 mmol) is then added dropwise, and after 30 min. the cooling bath is removed and the reaction is allowed to warm to room temperature. The reaction is quenched with water (5 mL), basified to pH 10 with 1N NaOH, and extracted with DCM. The combined organics are dried over Na2SO4, filtered, and concentrated. Purified on 40 g Redisep silica gel cartridge with 5% MeOH/DCM to give the title compound. 1H NMR (acetone-d6) δ 9.21 (s, 1H), 8.72 (dd, J=4.8, 1.7 Hz, 1H), 8.60 (br s, 1H), 8.36 (ddd, J=6.1, 1.9, 1.9 Hz, 1H), 7.58 (dd, J=8.0, 5.0, 0.8 Hz, 1H), 7.46-7.42 (m, 2H), 7.27-7.22 (m, 3H), 6.95 (d, J=7.6 Hz, 1H), 6.92 (t, J=2.2 Hz, 1H), 6.82 (ddd, J=8.1, 2.4, 0.9 Hz, 1H), 5.67 (d, J=4.7 Hz, 1H), 5.50 (dd, J=14.7, 5.8 Hz, 1H), 5.42 (dd, J=14.7, 3.9 Hz, 1H), 5.12 (ddd, J=5.8, 4.6, 4.0 Hz, 1H), HPLC-MS calculated C22H17ClN6O3 (M+H+) 449.1, found 449.0.

Provenance & Evidence