Potassium Carbonate → HCID 57988400, compound

HRID 2081135Notes

Reaction equation

HRID 2081135 reaction equation
[NH2:1][C@@H:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].C([O-])([O-])=O.[K+].[K+].Br[C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([F:27])[CH:18]=1.OS([O-])(=O)=O.[K+]>CC(N(C)C)=O.[Cu]I.C(OCC)C.O>[F:27][C:19]1[CH:18]=[C:17]([NH:1][C@@H:2]([C:6]([CH3:9])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])[CH:22]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:20]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 164608L-tert-LeucineHCID 516920Potassium bisulfateHCID 27363233-Bromo-5-fluorobenzotrifluoride

Product 1

HCID 57988400HCID 57988400, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

(S)-2-amino-3,3-dimethylbutanoic acid (0.50 g, 3.81 mmol), K2CO3 (1.580 g, 11.44 mmol), copper(I) iodide (0.073 g, 0.38 mmol) and 1-bromo-3-fluoro-5-(trifluoromethyl)benzene (2.32 g, 9.53 mmol) in DMA (4 mL) was heated at 95° C. for 32 hrs. H2O (15 mL) and ethyl ether (20 ml) was added. The aqueous phase was isolated and acidified with saturated KHSO4 solution, extracted with ether, dried over sodium sulfate. After removal of solvent, it gave (S)-2-(3-fluoro-5-(trifluoromethyl)phenylamino)-3,3-dimethylbutanoic acid (0.78 g, 70%) as white solid. LCMS (APCI−): 292.2. 1H NMR (400 MHz, d6-DMSO) δ 12.63 (s, 1H), 6.88 (s, 1H), 6.66 (d, J=12.4 Hz, 1H), 6.61 (d, J=8.8 Hz, 1H), 6.40 (d, J=9.2 Hz, 1H), 3.71 (d, J=9.6 Hz, 1H), 0.98 (s, 9H).

Workup

  1. customThe aqueous phase was isolated
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent, it

Sources & evidence

ORD record
ord-f8a46224443441c19083eff76cf8fe2c
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

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