Citric Acid → HCID 66732558, compound

HRID 2370354Notes

Reaction equation

HRID 2370354 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH3:11])=[O:7])=[C:4]([F:14])[CH:3]=1.[NH2:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18].C([O-])([O-])=O.[K+].[K+].C(C1CCCCC1=O)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.[Cu]I.O>[CH2:9]([NH:8][C:6]([C:5]1[CH:12]=[CH:13][C:2]([NH:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[CH:3][C:4]=1[F:14])=[O:7])[CH2:10][CH3:11]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 6119Aminoisobutyric acidHCID 11430Potassium CarbonateHCID 134002-AcetylcyclohexanoneHCID 246970544-Bromo-2-fluoro-N-propylbenzamide

Product 1

HCID 66732558HCID 66732558, compoundYield 148.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The title compound was prepared according to General Method 7. 4-bromo-2-fluoro-N-propylbenzamide (620 mg, 2.39 mmol), 2-aminoisobutyric acid (422 mg, 4.09 mmol), CuI (100 mg, 0.6 mmol), TEA (catalytic amount) and K2CO3 (1.13 g, 8.1 mmol) were dissolved in DMF (8 ml) and water (2 ml) stirred at RT for 5 min. Then 2-acetylcyclohexanone (0.13 g, 0.3 mmol) was added and the reaction mixture was heated at 100° C. for 18 h. The reaction mixture was acidified with 1 M citric acid (pH 4) and extracted with ethyl acetate (100 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 1.0 g of 2-(4-(propylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with ethyl acetate (100 mL, 2 times)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8f124fb902d4c609ab8150feb8ffa90
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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