Potassium Carbonate → HCID 54076025, compound

HRID 266391Notes

Reaction equation

HRID 266391 reaction equation
C([O-])([O-])=O.[K+].[K+].[Cl: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.CO>[C:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19](=[S:20])[C@@H:18]([NH:17][S:14]([C:11]2[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=2)(=[O:16])=[O:15])[CH2:34][CH2:35][CH3:36])=[CH:23][CH:24]=1)([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 54388402HCID 54388402, compound

Product 1

HCID 54076025HCID 54076025, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of K2CO3 (3.2 g) in water (40 ml) was added to a solution of (S)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-4-methylthiobutanamide (3.75 g) in methanol (80 ml), and 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 methanol completely that a small amount of purified water was added to the residue, and then the product 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 resulting crude product was recrystallized from acetonitrile to obtain (S)-N-(4-(carboxymethyl)phenyl)-2-(4-chlorobenzenesulfonylamino)-4-methylthiobutanamide (2.84 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove methanol completely that a small amount of purified water
  3. additionwas added to the residue
  4. concentrationthe product 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 resulting crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-9631ca5d20ef4e039cb58e9bfe73e732
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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