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

HRID 1602499노트

반응식

HRID 1602499 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-052087bbc78f4cbeb9a1418f8976e371
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05981559

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