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

HRID 1645241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645241
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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)benzene-sulfonyl 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 S-13 (11.32 g, 71%).

Aufarbeitung

  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 S-13 (11.32 g, 71%)

Quellen und Nachweise

ORD-Eintrag
ord-5eba2e5c760843a0a2312828b3de15f1
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124624B2

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