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

HRID 2388712Notes

Reaction equation

HRID 2388712 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-fce32808a1414b1e8ec81fbc976deeb2
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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