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

HRID 1602499ノート

反応式

HRID 1602499 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-052087bbc78f4cbeb9a1418f8976e371
出典データセット
uspto-grants-1999_11
特許番号
US05981559

反応ノート

読み込み中…