Methyl chloroformate → [Tert-butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-propynoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

LiHMDS (4.35 ml, 1 M in THF, 4.35 mmol) was added to a solution of ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (750 mg, 2.5 mmol, in dry THF (4.3 ml) under nitrogen at −78° C. The mixture was slowly warmed up to −40° C. and maintained at this temperature for 1 hour. The latter was then transferred dropwise via cannula to a solution of ClCO2Me (314 μl, 4.06 mmol) in THF (7.5 ml) at −40° C. The resulting mixture was allowed to return to RT. Saturated aqueous NH4Cl and AcOEt were added and the organic phase was extracted (3×15 ml AcOEt) and dried over Na2SO4. The title compound was obtained after purification by column chromatography (PE/AcOEt:80/20 to 75/25).

Provenance & Evidence