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

HRID 2388661노트

반응식

HRID 2388661 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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%

후처리

  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

출처 및 근거

ORD 기록
ord-6cf1f059ab4643b38a5d12a6e518c398
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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