Dimethylformamide → HCID 20651220, compound

Participants

Reaction Steps

To a solution of 2-phenyl benzoic acid (0.1 g) in tetrahydrofuran (2 ml), there was added, with ice-cooling, 0.075 g of thionyl chloride and a catalytic amount of N,N-dimethylformamide and the mixture was heated under reflux for 2 hours. After concentration of the reaction solution, the resulting acid chloride was dissolved in 3 ml of dichloromethane and the resulting solution was dropwise added to a solution of (11aS)-10-(4-aminobenzoyl)-1,2,3,10,11,11a-hexahydro-pyrrolo[1,2-b][1,2,5]benzothiadiazepin-5,5-dioxide (0.15 g) prepared in Reference Example 37 and pyridine (0.05 g) in dichloromethane (3 ml) at room temperature for 15 minutes. After stirring the reaction solution at room temperature for 3 hours, it was poured into ice water and then extracted with ethyl acetate. The resulting organic phase was washed with water and dried over anhydrous magnesium sulfate. After concentration of the organic phase, the resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/methanol (49/1) to thus give 0.05 g (yield 22.6%) of the title compound.

Provenance & Evidence