Hydrochloric Acid → HCID 20740244, compound

Participants

Reaction Steps

To a solution of (S)-4-cyano-4-({(1R,2S)-2-[(1-methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarbonyl}-amino)-butyric acid methyl ester (prepared as described in Example 3 using glutamic acid amide methyl ester) (572 mg, 1.35 mmol) in 15 mL of THF and 2 mL of MeOH was added a solution of lithium hydroxide hydrate (370 mg, 8.82 mmol) in 15 mL of water. The reaction mixture was stirred at room temp for 30 minutes, then poured into a slurry of ice and 20 mL of a 1N HCl solution. The organic layer was extracted with 50 mL of ethyl acetate, separated, washed with 50 mL of water, dried with sodium sulfate, and concentrated to give 556 mg (100%) of (S)-4-cyano-4-({(1R,2S)-2-[(1-methyl-1H-indole-2-carbonyl)-amino]-cyclohexanecarbonyl}-amino)-butyric acid as a white amorphous solid. MS: 409 (M−H+).

Provenance & Evidence