Methyl chloroformate → HCID 90387596, compound

Participants

Reaction Steps

A mixture of Example 6a (0.0145 g, 0.042 mmol) in N,N-dimethylacetamide (0.5 mL) was treated sequentially with methyl carbonochloridate (0.016 mL, 0.211 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.074 mL, 0.422 mmol) and stirred overnight at ambient temperature. The reaction mixture was then diluted with methanol (1.2 mL), treated with sodium carbonate (0.011 g, 0.105 mmol) and stirred at ambient temperature for 4 hours. The reaction mixture was partitioned between ethyl acetate and water and washed with saturated aqueous sodium chloride. The aqueous layers were combined and exhaustedly extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by reverse phase HPLC(C18, acetonitrile/water (0.1% TFA), 0-50%) to provide 0.0069 g (40.7%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.51 (s, 1H), 7.76 (d, J=1.53 Hz, 1H), 7.69 (s, 1H), 7.29 (m, 1H), 7.23 (m, 1H), 6.79 (s, 1H), 5.00 (d, J=15.56 Hz, 1H), 4.44 (m, 2H), 4.12 (s, 3H), 3.94 (d, J=15.26 Hz, 1H), 3.50 (s, 3H), 2.93 (s, 3H). MS (ESI+) m/z 402.1 (M+H)+.

Provenance & Evidence