Potassium Carbonate → N-[4-(trifluoromethyl)phenyl]-D-valine

HRID 1360381Notes

Reaction equation

HRID 1360381 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1.[NH2:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+]>[Cu]I.CC(N(C)C)=O>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 71563D-Valine

Product 1

HCID 13388455N-[4-(trifluoromethyl)phenyl]-D-valineYield 46%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Trifluoromethyliodobenzene (0.27 g, 1.0 mmol), D-valine (0.12 g, 1.0 mmol), potassium carbonate (0.21 g, 1.5 mmol), copper(I) iodide (19 mg, 0.10 mmol) and dimethylacetamide (1 mL) were charged in a threaded test tube, and the mixture was stirred with heating at 90° C. for 2 days. After work-up according to a conventional method, the object product was eluted by silica gel column chromatography (20% to 40% mixed solvent of ethyl acetate/hexane) to give the title compound (0.12 g, 0.46 mmol, 46%).

Workup

  1. washthe object product was eluted by silica gel column chromatography (20% to 40% mixed solvent of ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d86dc61b48047b8821d5e8bd40643cf
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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