Hydrochloric Acid → HCID 20740209, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. suspension of (S)-2-({(1R,2S)-2-[(1-Methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarbonyl}-amino)-pentanedioic acid diamide (0.53 g, 1.2 mmol) in 30 mL of anhydrous pyridine and 30 mL of CH2Cl2 was slowly added trifluoroacetic anhydride dropwise. The resulting yellow reaction mixture was stirred at 0° C. for 15 min, and poured into a slurry of ice and a 1N HCl solution. The mixture was extracted with 250 mL of ethyl acetate, washed with a 1N solution of HCl (3×250 mL), water (250 mL), and dried with sodium sulfate, filtered, concentrated and purified by column chromatography (5:95, MeOH/CH2Cl2) to give 430 mg (89%) of 1-methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-(1,3-dicyano-propylcarbamoyl)-cyclohexyl]-amide as a light-yellow liquid, which was determined to be a 38:62 ratio of epimers by 1H NMR spectroscopy. MS: 392 (M+H+).

Provenance & Evidence