Sodium Hydroxide → 1-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopent-3-ene carboxylic acid

HRID 481391ノート

反応式

HRID 481391 の反応式
C([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH2:16][N:17]3[C:21]4=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]4[N:19]=[C:18]3[CH2:28][CH3:29])=[CH:14][CH:15]=2)[CH2:10][CH:9]=[CH:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[CH2:28]([C:18]1[N:17]([CH2:16][C:13]2[S:12][C:11]([C:6]3([C:4]([OH:5])=[O:3])[CH2:10][CH:9]=[CH:8][CH2:7]3)=[CH:15][CH:14]=2)[C:21]2=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]2[N:19]=1)[CH3:29]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 684276321-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)-thiophen-2-yl]cyclopent-3ene carboxylic acid ethyl ester2 回

生成物 1

HCID 190662441-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)thiophen-2-yl]cyclopent-3-ene carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of the product of Step 5, above (6), in methanol was added an excess of 2N NaOH. The reaction mixture was heated to 80° C. for 1 hour, cooled to room temperature and the solvent evaporated. Water was added to the residue and the solution was extracted 2 times with EtOAc. The aqueous layer was acidified with 10% HCl and the resultant white suspension was extracted 2 times with EtOAc. The organics were dried over MgSO4, filtered and concentrated to a solid. The solid was crystallized from EtOAc to yield the title compound (8).

後処理

  1. temperaturecooled to room temperature
  2. customthe solvent evaporated
  3. additionWater was added to the residue
  4. extractionthe solution was extracted 2 times with EtOAc
  5. extractionthe resultant white suspension was extracted 2 times with EtOAc
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customThe solid was crystallized from EtOAc

出典と根拠

ORDレコード
ord-9031c5cc868a412a889a909539eeb33c
出典データセット
uspto-grants-1998_08
特許番号
US05789415

反応ノート

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