Methyl iodide → HCID 59900509, compound

Participants

Reaction Steps

A mixture of methyl iodide (98 ml, 1.57 mmol), benzyl 3-{(1R/S)-1-[(tert-butoxycarbonyl)amino]-2-hydroxyethyl}phenethylcarbamate (preparation 119) (590 mg, 1.4 mmol), benzyltriethylammonium chloride (325 mg, 1.4 mmol) and NaOH solution (185 ml, 10M, 1.85 mmol) in dichloromethane (10 ml), was stirred at room temperature for 3 days. The reaction mixture was partitioned between dichloromethane and water, the phases separated, and the organic layer dried over MgSO4 and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (0:100 to 50:50) to provide the title compound as a colourless oil, (289 mg, 47%).

Provenance & Evidence