Hydrochloric Acid → 4-[Methyl-[[3-(trifluoromethyl)phenyl]sulfonyl]-amino]-butyric acid

HRID 1881680노트

반응식

HRID 1881680 반응식
Cl.[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[OH-].[K+].[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.Cl>O.C1COCC1.C(Cl)Cl>[CH3:2][N:3]([S:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:24])[F:25])[CH:15]=1)(=[O:22])=[O:21])[CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 126266544-(Methylamino)butyric acid hydrochloride

생성물 1

HCID 432364554-[Methyl-[[3-(trifluoromethyl)phenyl]sulfonyl]-amino]-butyric acid

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

4-(Methylamino)butanoic acid hydrochloride (10, 15.1 g, 98.1 mmol) was added to a solution of KOH (16.5 g, 294 mmol) in H2O (75 ml) and the reaction mixture was cooled in an ice bath. A solution of 3-(trifluoromethyl)benzenesulfonyl chloride (9, 12.0 g, 49.1 mmol) in THF (75 ml) was added dropwise to the reaction mixture and the mixture was stirred at room temperature overnight. Aqueous 6 M HCl (75 ml) was added, while cooling with an ice bath, and the addition of CH2Cl2 then followed. The organic phase was separated, washed with sat. NaCl solution, dried over Na2SO4 and concentrated and the residue was co-evaporated with a minimal amount of diethyl ether. Recrystallization of the residue from ethyl acetate/heptane gave AC-13 (11.32 g, 71%).

후처리

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. temperaturewhile cooling with an ice bath
  3. customThe organic phase was separated
  4. washwashed with sat. NaCl solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customRecrystallization of the residue from ethyl acetate/heptane
  8. customgave AC-13 (11.32 g, 71%)

출처 및 근거

ORD 기록
ord-9dd01cbddaad4526b78311ea808ed479
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318769B2

반응 노트

불러오는 중…