Methyl chloroformate → HCID 86680526, compound

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Reaction Steps

A solution of the product from Example 180 (50 mg, 0.089 mmol) in 1,4-dioxane (0.5 mL) and 4 N HCl in 1,4-dioxane (0.5 mL, 2.00 mmol) was stirred at room temperature for 90 minutes and then concentrated in vacuo. Dichloromethane (1 mL) was added to the residue, followed by methyl chloroformate (7.6 μL, 0.098 mmol) and triethylamine (0.062 mL, 0.445 mmol). The resulting solution was stirred at room temperature for 90 minutes. The mixture was partitioned between water and dichloromethane (3×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-10% methanol in dichloromethane. The title compound was obtained as a semi-solid (18 mg, 39%). 1H NMR (300 MHz, CDCl3) δ ppm 0.82-1.02 (m, 4 H) 1.18-3.31 (m, 9 H) 3.50-3.89 (m, 5 H) 4.54-4.82 (m, 1 H) 5.17-5.38 (m, 1 H) 5.56-5.72 (m, 1 H) 6.25-6.41 (m, 1 H) 7.40-7.69 (m, 4 H) 7.85-8.05 (m, 2 H); MS (ESI) m/z 520 (M+H)+.

Provenance & Evidence