Diisopropylethylamine → 10-[(2'-Methoxy-2-methyl-[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid (2,3-dihydroxy-propyl)-methyl-amide

Participants

Reaction Steps

To a solution of 10-[(2′-methoxy-2-methyl-[1,1′-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H— pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Step E (0.50 g, 1.10 mmol) and 3-methylamino-1,2-propanediol (0.14 mL, 1.33 mmol) in N,N-dimethylformamide (4 mL) was added 1-hydroxybenzotriazole monohydrate (0.16 g, 1.18 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.23 g, 1.20 mmol) followed by N,N-diisopropylethyl amine (0.29 mL, 1.66 mmol). The reaction mixture was stirred overnight, diluted with ethyl acetate and washed with water and saturated aqueous sodium bicarbonate. The organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow oil. Purification by flash chromatography using a solvent system of 3% methanol in chloroform gave a white foam which was crystallized by trituration with diethyl ether-hexane to provide 0.11 g of title product as a white amorphous solid.

Provenance & Evidence