Sodium Hydroxide → tert-butyl 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetate

HRID 2388661ノート

反応式

HRID 2388661 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH:16]1[CH2:18][CH2:17]1)[CH2:13][CH2:14][OH:15])(=[O:11])=[O:10].[OH-].[Na+].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:13][CH2:14][O:15][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:16]1[CH2:18][CH2:17]1)(=[O:11])=[O:10]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 579162662-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-6-methylbenzenesulfonamide

生成物 1

HCID 57916276tert-butyl 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetate収率 70%

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a cold solution of 2-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-6-methylbenzenesulfonamide (1 eq.) in dichloromethane (15 ml) was added tetrabutylammonium chloride (0.1 eq.) and 35% sodium hydroxide solution (15 ml) at 0° C. tert-Butyl 2-bromoacetate (1.2 eq.) was added dropwise to this cold reaction mixture maintaining the same temperature. After addition was complete, the reaction mixture was stirred at room temperature for 16 h (monitored by TLC). It was diluted with dichloromethane and the organic layer was washed with water and brine and finally dried over sodium sulfate. Evaporation of the organic layer under reduced pressure gave the crude product which was purified by column chromatography (20% ethyl acetate in hexane). Yield: 70%

後処理

  1. additionwas added dropwise to this cold reaction mixture
  2. temperaturemaintaining the same temperature
  3. additionAfter addition
  4. washthe organic layer was washed with water and brine
  5. dry with materialfinally dried over sodium sulfate
  6. customEvaporation of the organic layer under reduced pressure

出典と根拠

ORDレコード
ord-6cf1f059ab4643b38a5d12a6e518c398
出典データセット
uspto-grants-2012_09
特許番号
US08268814B2

反応ノート

読み込み中…