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

HRID 1881680ノート

反応式

HRID 1881680 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-9dd01cbddaad4526b78311ea808ed479
出典データセット
uspto-grants-2012_11
特許番号
US08318769B2

反応ノート

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