Hydrochloric Acid → 4-[Methyl-[[3-(trifluoromethyl)phenyl]sulfonyl]-amino]-butyric acid
Reaction equation
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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
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%).
Workup
- temperaturethe reaction mixture was cooled in an ice bath
- temperaturewhile cooling with an ice bath
- customThe organic phase was separated
- washwashed with sat. NaCl solution
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customRecrystallization of the residue from ethyl acetate/heptane
- customgave AC-13 (11.32 g, 71%)
Sources & evidence
- ORD record
- ord-9dd01cbddaad4526b78311ea808ed479
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08318769B2
Reaction notes
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