Hydrochloric Acid → HCID 70245873, compound

Participants

Reaction Steps

To a solution of (2R,11aR)-2-hydroxy-10-[4-[(2-phenylbenzoyl)amino]benzoyl]-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.4 g) prepared in Example 45 and obtained in the form of free base in dimethyl sulfoxide (8 ml), there was added, at room temperature, 1.6 g of N,N′-dicyclohexyl carbodiimide and 0.135 g of trifluoroacetic acid. After stirring the reaction solution at room temperature for 15 hours, a 6N hydrochloric acid solution was added thereto and the reaction solution was stirred for additional 30 minutes. The precipitates separated out were filtered off and washed with water. The filtrate and the wash liquid were combined, the mixture was alkalified with a saturated aqueous solution of sodium carbonate and then extracted with ethyl acetate. The resulting organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was subjected to silica gel column chromatography and then eluted with chloroform/acetone (4/1) to thus give 0.23 g of (11aR)-10-[4-[(2-phenylbenzoyl)amino]benzoyl]-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-2-one in the form of amorphous powder. The resulting amorphous powder (0.23 g) was dissolved in ethyl acetate and 0.12 ml of a 4N hydrochloric acid-ethyl acetate solution was added to the resulting solution at room temperature. After stirring the mixture at room temperature for one hour, the resulting precipitates separated out were recovered by filtration, followed by washing them with ethyl acetate and then dried to thus give 0.15 g (yield 34.2%) of the title compound.

Provenance & Evidence