Acetic Anhydride → HCID 68194652, compound

Participants

Reaction Steps

To a solution of Example 109B (200 mg, 0.397 mmol) in 5 mL N,N-dimethylformamide was added diisopropylethylamine (0.346 ml, 1.983 mmol) followed by acetic anhydride (0.041 ml, 0.436 mmol). The reaction mixture was stirred at room temperature overnight, then diluted with ethyl acetate. The organics were washed with saturated aqueous NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated. The crude material was purified by chromatography was performed with an Analogix 280 with an SF 25-40 column, 0% to 4% methanol/dichloromethane gradient over 30 minutes to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 1.02 (d, J=8.14 Hz, 4H) 2.10 (d, J=21.70 Hz, 3H) 3.46-3.64 (m, 2H) 4.75 (s, 2H) 6.75-7.04 (m, 1H) 7.12 (s, 1H) 7.44-7.90 (m, 6H) 9.16 (s, 1H) 10.80 (s, 1H). MS (ESI+) m/z 546.2 (M+H)+.

Provenance & Evidence