Citric Acid → 4-[3-(4-Chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetic acid

HRID 1602499Notes

Reaction equation

HRID 1602499 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[C:16]([NH:27][C:28](=[O:48])[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=[CH:36][C:37]4[S:38][CH:39]=[C:40]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[N:41]=4)[CH:30]=3)[CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][CH2:13][C:14]2[CH:26]=[CH:25][C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[C:16]([NH:27][C:28](=[O:48])[C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=[CH:36][C:37]4[S:38][CH:39]=[C:40]([C:42]5[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=5)[N:41]=4)[CH:30]=3)[CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 311Citric AcidHCID 54512577Ethyl 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetate

Product 1

HCID 539849484-[3-(4-Chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetic acidYield 83.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetate (0.30 g, 0.43 mmol) was dissolved in a mixed solution of tetrahydrofuran (10 ml) and methanol (5 ml), 1 N sodium hydroxide aqueous solution (1.0 ml) was added to the solution, and the mixture was subjected to 12 hours of reaction. The reaction solution was acidified by adding ice and 10% citric acid aqueous solution, and the product formed was extracted three times with chloroform. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. By crystallizing the resulting residue from chloroform-acetonitrile, 4-[3-(4-chlorophenylsulfonyl)propyl]-2-[3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoylamino]phenoxyacetic acid (0.24 g, 0.36 mmol, 83%) was obtained as colorless crystals.

Workup

  1. additionwas added to the solution
  2. customthe mixture was subjected to 12 hours of reaction
  3. customthe product formed
  4. extractionwas extracted three times with chloroform
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customBy crystallizing the resulting residue from chloroform-acetonitrile

Sources & evidence

ORD record
ord-052087bbc78f4cbeb9a1418f8976e371
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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