Potassium Hydroxide → [4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid

HRID 858074ノート

反応式

HRID 858074 の反応式
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:21])(=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:8][CH:7]=1)C.[OH-].[K+]>C(O)C>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:22])=[O:3])=[CH:7][CH:8]=1)(=[O:20])=[O:21]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 58762849[4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid ethyl ester

生成物 1

HCID 24267818[4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid収率 65.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid ethyl ester (0.26 g, 0.813 mmol) in absolute ethanol (10 mL) was treated with a 1.0M ethanolic potassium hydroxide solution (2.0 mL, 2.0 mmol). The reaction mixture was heated to reflux under argon for 3.5 h. The reaction mixture was then concentrated in vacuo. The residue was dissolved in water and filtered through celite. The filtrate was acidified to pH=4.5 with a 1.0M aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to afford [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid (155 mg, 65%) as an off white solid; 1H NMR (DMSO-d6, 300 MHz) δH 12.26 (broad s, 1H), 7.96 (d, J=4.4 Hz, 1H), 7.77 (d, J=7.7 Hz, 2H), 7.80 (t, J=7.5 Hz, 1H), 7.37 (d, J=7.7 Hz, 2H), 7.13 (d, J=8.8 Hz, 1H), 6.82 (broad s, 1H), 3.62 (s, 2H); LRMS for C13H12N2O4S (M+H)+ at m/z=293.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under argon for 3.5 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. filtrationfiltered through celite
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-1999cab57aa548be94fb6fc5cbb5e8d5
出典データセット
uspto-grants-2006_12
特許番号
US07148229B2

反応ノート

読み込み中…