Pyridine → HCID 178483592, compound

Participants

Reaction Steps

4′-(1-(Isopropoxycarbonyl)cyclopropyl)biphenyl-4-carboxylic acid (9.2 g, 28 mmol), dichloroethane (50 mL), DMF (0.1 mL), thionyl chloride (5.5 mL, 62 mmol) were heated to 75° C. for 1.5 hours. (acid chloride formation was monitored by adding small aliquot (100 μL) to a solution of benzyl amine in acetonitrile and analyzing for the benzyl amide by LCMS; no starting material was observed by LCMS). The solution was evaporated on a rotavap and THF (10 mL) was added. The solution of the acid chloride in THF was added via syringe to a solution of 3-methylamino-but-2-enoic acid methyl ester (4.0 g, 31.2 mmol) and pyridine (5.5 mL, 70 mmol) in THF (50 mL). The solution was stirred at room temperature overnight. The volatiles were evaporated on a rotavap to yield the crude product.

Provenance & Evidence