Methyl chloroformate → HCID 136403684, compound

Participants

Reaction Steps

To a solution of Example 173 (0.079 mmol) in dry dichloromethane (1 mL) at 0° C. was added methylchloroformate (0.12 mL, 1.55 mmol) and triethylamine (33 μL, 0.24 mmol). The resulting mixture was stirred at rt 3 h and partitioned between H2O (5 mL) and dichloromethane (3×5 mL). The combined organic layers were dried over Na2SO4, the drying agent was filtered off, and the solvent was removed in vacuo. To a solution of the resulting residue in methanol (1 mL) was added K2CO3, and the resulting mixture was stirred at rt 90 min. The mixture was partitioned between N HCl (5 mL) and ethyl acetate (3×5 mL), and the combined organic layers were dried over Na2SO4. The crude product was purified by column chromatography on silica gel using 5% methanol in chloroform, and the title compound was obtained as a lt. yellow solid (48 mg, 88%): 1H NMR (300 MHz, DMSO-d6) δ 0.43 (m, 1 H), 0.67 (m, J=6.62 Hz, 3 H), 0.71 (d, J=6.62 Hz, 3 H), 0.89 (m, 2 H), 1.33 (m, 1 H), 1.45 (m, 3 H), 1.67 (m, 1 H), 2.10 (m, 1 H), 2.40 (m, 1 H), 2.70 (m, 1 H), 3.02 (s, 3 H), 3.74 (m, 1 H), 3.93 (m, 1 H), 4.13 (m, 1 H), 7.16 (m, 1 H), 7.49 (m, 5 H), 8.12 (m, 1 H), 10.01 (s, 1 H), 14.54 (br s, 1 H); MS (ESI) m/z=689 [M+H].

Provenance & Evidence