N-Methyl-D-glucamine → 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 methyl-[(2S,3R,4R, 5R)-2,3,4,5,6-pentahydroxy-hexyl)-amide

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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 Example 14, Step E (0.70 g, 1.55 mmol), N-methyl-D-glucamine (0.36 g, 1.84 mmol) and 1-hydroxybenzotriazole monohydrate (0.23 g, 1.72 mmol) in N,N-dimethylformamide (6 mL) wad added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.33 g, 1.72 mmol) followed by N,N-diisopropylethyl amine (0.41 mL, 2.30 mmol). The reaction mixture was stirred overnight, then was 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 foam. Purification by flash chromatography on silica gel using a solvent system of 10% methanol in chloroform provided the title compound, which was redissolved in dichloromethane and evaporated to dryness in vacuo to a pale, yellow foam (0.63 g).

Provenance & Evidence