4-Hydroxymethylpyridine → 2-[(Benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid pyridin-4-ylmethyl ester

Participants

Reaction Steps

To a mixture of 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (150 mg), triphenylphosphine (120 mg), 4-pyridinemethanol (51 mg) and THF (3.0 ml) was added diethyl azodicarboxylate toluene solution (40%, 210 μl) at 0° C. with stirring and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by medium pressure preparative LC (hexane/ethyl acetate=1/1-1/3) to give 2-[(benzyloxycarbonyl)(methyl)amino]-6-chloro-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid pyridin-4-ylmethyl ester.

Provenance & Evidence