Potassium Carbonate → HCID 54302242, compound

HRID 266392Notes

Reaction equation

HRID 266392 reaction equation
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]([CH2:34][CH2:35][CH3:36])[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31]CC)=[O:30])=[CH:24][CH:23]=2)=[S:20])(=[O:16])=[O:15])=[CH:10][CH:9]=1>O.C(O)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17][C@@H:18]([CH2:34][CH2:35][CH3:36])[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:24][CH:23]=2)=[S:20])(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 53793533HCID 53793533, compound

Product 1

HCID 54302242HCID 54302242, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of K2CO3 (962 mg) in water (15 ml) was added to a solution of (S)-2-(4-bromobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-4-methylthiobutanamide (1.23 g) in ethanol (50 ml). The whole was stirred at room temperature overnight under argon. The reaction mixture was concentrated under reduced pressure. It was repeated 3 times in order to remove ethanol completely that a small amount of purified water was added to the residue, and then the mixture was concentrated under reduced pressure. The residue was dissolved in purified water and washed with ethyl acetate. The aqueous layer was acidified with 1N HCl, and then extracted with ethyl acetate. The combined ethyl acetate layers were washed with a saturated saline solution and dried over Na2SO4. Then, the solvent was evaporated under reduced pressure and the crude product was recrystallized from acetonitrile to obtain (S)-2-(4-bromobenzenesulfonylamino)-N-(4-(carboxymethyl)phenyl)-4-methylthiobutanamide (800 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove ethanol completely that a small amount of purified water
  3. additionwas added to the residue
  4. concentrationthe mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in purified water
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washThe combined ethyl acetate layers were washed with a saturated saline solution
  9. dry with materialdried over Na2SO4
  10. customThen, the solvent was evaporated under reduced pressure
  11. customthe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-035a18b6753b4c179b9411e848885cf7
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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