Triethylamine → HCID 18612764, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 1.0 g (2.66 mmol) of 4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate from Reference Example 12 and 1.85 ml (13.3 mmol) of triethylamine in 8 ml of CH2Cl2 was added 1.17 g (6.65 mmol) of 2,4-dimethoxybenzoyl chloride. The mixture was stirred at room temperature overnight, diluted with CH2Cl2 and washed with 2 N citric acid. The organic layer was washed with H2O, 1 N Na2CO3, brine and dried over Na2SO4. The solvent was removed and the residue was chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as an eluent to give 1.0 g of methyl 1-(2,4-dimethoxybenzoyl)-4-(4-methoxybenzenesulfonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate as a white foam. Anal. for C27H28H2O8S: Calc'd: C, 60.0; H, 5.2; N, 5.2; Found: C, 60.0; H, 5.2; N, 5.1.

Provenance & Evidence