Hydrochloric Acid → HCID 11271434, compound

HRID 2111021Notes

Reaction equation

HRID 2111021 reaction equation
C([O:4][C@H:5]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:23]([NH:24][C:25]([O:27][CH:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[CH3:29])=[O:26])=[CH:22][O:21][N:20]=2)=[CH:15][CH:14]=1)=[O:11])[C:6]([OH:8])=[O:7])(=O)C.[OH-].[Na+].Cl>CO>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH:28]([O:27][C:25]([NH:24][C:23]1[C:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10](=[O:11])[CH2:9][C@@H:5]([OH:4])[C:6]([OH:8])=[O:7])=[CH:14][CH:15]=2)=[N:20][O:21][CH:22]=1)=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11226088HCID 11226088, compound

Product 1

HCID 11271434HCID 11271434, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R)-2-Acetoxy-4-[(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}phenyl)amino]-4-oxobutanoic acid (132 mg, 0.256 mmol) was dissolved in methanol (2.5 ml), 1N aqueous sodium hydroxide solution (2.5 ml) was added, and the mixture was stirred at room temperature for 1 hour. 1N Hydrochloric acid (2.6 ml) was added at 0° C. to weak-acidify the reaction system, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (111 mg, 92%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1dc1e79ee1b64039975e10c317f0854d
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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