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

HRID 2388712ノート

反応式

HRID 2388712 の反応式
[OH-].[K+].Cl.[CH3:4][NH:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[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>[CH3:4][N:5]([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])[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

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

To a solution of KOH (16.5 g, 294 mmol) in H2O (75 ml) was added 4-(methylamino)butyric acid hydrochloride (10, 15.1 g, 98.1 mmol) and the reaction mixture was cooled with an icebath. A solution of 3-(trifluoromethyl)benzenesulfonyl chloride (9, 12.0 g, 49.1 mmol) in THF (75 ml) was dropwise added to the reaction mixture and stirring was continued at room temperature overnight. Aqueous 6 M HCl (75 ml) was added to the reaction mixture while cooling with an icebath, after which CH2Cl2 was added. The organic layer was separated, washed with brine, dried (Na2SO4), concentrated and co-evaporated with a minimal amount of Et2O. Crystallization of the residue out of EtOAc/heptane resulted in AC-08 (11.32 g, 71%).

後処理

  1. temperaturethe reaction mixture was cooled with an icebath
  2. temperaturewhile cooling with an icebath
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated and co-evaporated with a minimal amount of Et2O
  7. customCrystallization of the residue out of EtOAc/heptane
  8. customresulted in AC-08 (11.32 g, 71%)

出典と根拠

ORDレコード
ord-fce32808a1414b1e8ec81fbc976deeb2
出典データセット
uspto-grants-2012_09
特許番号
US08268814B2

反応ノート

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