Methyl chloroformate → HCID 23147119, compound

Participants

Reaction Conditions

Reaction Steps

Compound 69 (0.12 g, 0.41 mmol) obtained in Example 69 was dissolved in tetrahydrofuran (10 mL), triethylamine (0.15 mL, 1.1 mmol) was added thereto, and the solution was cooled to 4° C. Then, methyl chlorocarbonate (0.081 mL, 1.1 mmol) was added thereto, and the mixture was stirred for 2 hours with heating up to room temperature. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting methyl 2-acetyl-3,5-bis(methoxycarbonyloxy)-6-phenylphenylacetate was dissolved in a mixed solvent of tetrahydrofuran (5.0 mL) and water (5.0 mL), then the solution was cooled to 4° C., and sodium borohydride (73 mg, 1.9 mmol) was added thereto, taking 5 minutes, and then stirred for 1 hour. Water (10 mL) was added to the reaction mixture, and stirred for 10 minutes, and then extracted twice with ethyl acetate (0.10 L). The organic layer was washed with aqueous saturated sodium chloride solution, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (ethyl acetate/n-hexane=1/2) to obtain methyl 6-ethyl-3-hydroxy-5-(methoxycarbonyloxy)-2-phenylphenylacetate (89 mg, 64%).

Provenance & Evidence