Benzoyl chloride → HCID 59785894, compound

Participants

Reaction Steps

To a solution of the product of Step B (35.6 mg, 0.08 mmol) and NEt3 (43 μL, 0.31 mmol) in 10 mL of CH2Cl2 was added benzoyl chloride (20 μL, 0.17 mmol). After stirring at rt for 1 h, 2.0 mL of CH3OH and 100 μL of 5.0 N NaOH was added to the reaction mixture. After stirring for 30 min, the reaction mixture was partitioned between EtOAc (20 mL) and saturated aq NaHCO3 (20 mL). The organic layer was separated and washed with brine (20 mL). After the phases separated, the organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using 7:3 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.50 (s, 3H), 1.56 (s, 3H), 1.96 (t, J=12.4, 1H), 2.36 (dd, J=6.4, 13.2, 1H), 5.73 (m, 2H), 6.61 (d, J=8.7, 1H), 7.02 (d, J=8.5, 2H), 7.13 (d, J=8.5, 2H), 7.14-7.55 (m, 6H), 7.72-7.83 (m, 5H).

Provenance & Evidence