Citric Acid → HCID 66732569, compound

HRID 2370352Notes

Reaction equation

HRID 2370352 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])=[C:4]([F:15])[CH:3]=1.[NH2:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19].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:13]=[CH:14][C:2]([NH:16][C:17]([CH3:22])([CH3:21])[C:18]([OH:20])=[O:19])=[CH:3][C:4]=1[F:15])=[O:7])[CH2:10][CH2:11][CH3:12]

Participants

9

Reactant 5

HCID 311Citric AcidHCID 6119Aminoisobutyric acidHCID 11430Potassium CarbonateHCID 134002-AcetylcyclohexanoneHCID 24708843HCID 24708843, compound

Product 1

HCID 66732569HCID 66732569, compoundYield 94.3%

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-N-butyl-2-fluorobenzamide (950 mg, 3.22 mmol), 2-aminoisobutyric acid (450 mg, 4.36 mmol), CuI (100 mg, 0.5 mmol), TEA (0.1 mL) and K2CO3 (1.0 g, 7.2 mmol) were charged in DMF (8 ml) and water (2 ml) and stirred at RT for 5 min. 2-acetylcyclohexanone (100 mg, 0.7 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 (50 mL, 2 times). The combined organic layer was dried over Na2SO4 and concentrated to obtain 900 mg of 2-(4-(butylcarbamoyl)-3-fluorophenylamino)-2-methylpropanoic acid.

Workup

  1. customThe title compound was prepared
  2. extractionextracted with ethyl acetate (50 mL, 2 times)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d2b32dab02349978499b37fff0d2ab8
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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