Dimethylformamide → (11aS)-10-[4-[(2-Phenylbenzoyl) Amino]Benzoyl]-1,2,3,10,11, 11a-Hexahydro-5H-Pyrrolo[2,1-c][1,4]Benzodiazepin-5-One

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Reaction Steps

To a solution of 4-[(2-phenylbenzoyl)amino]benzoic acid (1.44 g) in tetrahydrofuran (10 ml), there were added, with ice-cooling, 0.62 g of thionyl chloride and a catalytic amount of N,N-dimethylformamide and the mixture was stirred at room temperature for one hour. After concentration of the reaction solution, the resulting acid chloride was dissolved in 10 ml of tetrahydrofuran and the resulting solution was dropwise added to a solution of (11aS)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (4 g) prepared in Reference Example 24 and triethylamine (0.5 g) in tetrahydrofuran (10 ml) with ice-cooling. The reaction solution was stirred for 2 hours under ice-cooling and it was concentrated and dissolved in ethyl acetate. The resulting organic phase was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained after concentration of the reaction solution was subjected to silica gel column chromatography and then eluted with chloroform/ethyl acetate (100/1) to thus give 0.89 g (yield 44.4%) of the title compound.

Provenance & Evidence