Hydrochloric Acid → HCID 20740244, compound

HRID 1883135Notes

Reaction equation

HRID 1883135 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][C@@H:6]([C:29]#[N:30])[NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:9].O.[OH-].[Li+].Cl>C1COCC1.CO.O>[C:29]([C@@H:6]([NH:7][C:8]([C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:9])[CH2:5][CH2:4][C:3]([OH:31])=[O:2])#[N:30]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 60083628HCID 60083628, compound

Product 1

HCID 20740244HCID 20740244, compoundYield 100.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  1. extractionThe organic layer was extracted with 50 mL of ethyl acetate
  2. customseparated
  3. washwashed with 50 mL of water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f8eff59c0f14eff91c0ae07d636b161
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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