Sodium borohydride → HCID 59485822, compound

Participants

Reaction Steps

A solution of ethyl 2-(2-(((4S,5S)-3-(4-chlorophenyl)-4-(3-methoxyphenyl)-2-oxooxazolidin-5-yl)methyl)-2H-tetrazol-5-yl)acetate (50 mg, 0.11 mmol) [Example 379] in MeOH (1 mL) is treated with excess sodium borohydride at room temperature for 30 min. The reaction is quenched with 1 mL 0.1 M HCl and extracted with EtOAc (3×5 mL). The combined organics are dried over MgSO4, filtered and concentrated to give the title compound. 1H NMR (acetone-d6, 400 MHz) δ 7.47-7.43 (m, 2H), 7.33-7.29 (m, 3H), 7.04 (app t, J=2.0 Hz, 1H), 7.00-6.98 (app d, J=7.7 Hz, 1H), 6.90 (ddd, J=8.3, 2.6, 0.9 Hz, 1H), 5.60 (d, J=5.2 Hz, 1H), 5.33 (dd, J=14.6, 6.2 Hz, 1H), 5.25 (dd, J=14.6, 4.1 Hz, 1H), 4.99 (ddd, J=6.2, 5.2, 4.1 Hz, 1H), 3.89-3.76 (m, 6H), 2.99 (t, J=6.3 Hz, 2H), HPLC-MS calculated C20H20ClN5O4 (M+H+) 430.1, found 430.1.

Provenance & Evidence