Triethylamine → (RS) Methyl 3-{6-[2-(3-acetoxy-4-nitrophenyl)-acetylamino]-pyridin-3-yl}-butanoate

Participants

Reaction Conditions

Reaction Steps

A solution of (RS) methyl 3-(6-amino-pyrid-3-yl)-butanoate (3.26 g, Reference Example 19) in dichloromethane (20 mL) at 10° C. was treated dropwise with a solution of (3-acetoxy-4-nitrophenyl)-acetyl chloride (4.32 g, Reference Example 17) in dichloromethane (30 mL) over 5 minutes. The mixture was stirred at 10° C. for a further 5 minutes then treated dropwise with triethylamine (2.47 mL) over 5 minutes. The resulting dark solution was stirred at room temperature for 1 hour, then left to stand overnight, then subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (3:2, v/v) to give the title compound (5.9 g) as a viscous gum.

Provenance & Evidence