2-Mercapto-2-methylpropanoic acid → 2-{[2-(3,5-Difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid

HRID 1866608Notes

Reaction equation

HRID 1866608 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5](=[O:8])[CH2:6]Br.C(=O)(O)[O-].[Na+].[SH:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21]>C1COCC1.O.C(OCC)C.Cl>[F:1][C:2]1[CH:3]=[C:4]([C:5](=[O:8])[CH2:6][S:18][C:19]([CH3:24])([CH3:23])[C:20]([OH:22])=[O:21])[CH:9]=[C:10]([F:12])[CH:11]=1

Participants

8

Reactant 3

HCID 784212-Mercapto-2-methylpropanoic acidHCID 516892Sodium BicarbonateHCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanone

Product 1

HCID 669733052-{[2-(3,5-Difluorophenyl)-2-oxoethyl]thio}-2-methylpropanoic acid

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-difluorophenacyl bromide (845 mg, 3.60 mmol) in THF (12 mL) and water (12 mL) was added sodium bicarbonate (317 mg, 3.78 mmol) and 2-mercaptoisobutyric acid (432 mg, 3.60 mmol). The reaction mixture was allowed to stir at ambient temperature for 1.0 h under a stream of nitrogen. The reaction mixture was diluted with diethyl ether (50 mL) and 1 M HCl (15 mL). The organic layer was then washed with 20 mL saturated brine. The organics were then dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound, which was used without further purification. MS: m/z=229 (M−CO2H).

Workup

  1. washThe organic layer was then washed with 20 mL saturated brine
  2. dry with materialThe organics were then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49e89eca02ac408497475da47ed5bce4
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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