Citric Acid → HCID 67343467, compound

HRID 1673452Notes

Reaction equation

HRID 1673452 reaction equation
[CH:1]1[CH2:5][CH2:4][CH2:3][CH:2]=1.C([O-])(=O)C.[K+].[C:11]([NH:19][C:20]1[CH:32]=[C:31](I)[CH:30]=[CH:29][C:21]=1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[C:11]([NH:19][C:20]1[CH:32]=[C:31]([CH:1]2[CH2:5][CH2:4][CH:3]=[CH:2]2)[CH:30]=[CH:29][C:21]=1[C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 311Citric AcidHCID 8882Cyclopentene2×HCID 517044Potassium Acetate2×HCID 67342064HCID 67342064, compound

Product 1

HCID 67343467HCID 67343467, compound

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalyst2×HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

0.21 mL of cyclopentene, 0.14 g of potassium acetate, 0.13 g of tetrabutylammonium chloride, 3.1 mg of triphenylphosphine and 2.7 mg of palladium acetate were added to 1.0 mL of N-dimethylformamide solution containing 0.20 g of tert-butyl 2-(benzamido)-4-iodobenzoate at room temperature and stirred under nitrogen atmosphere at the same temperature for 17 hours. 0.21 mL of cyclopentene, 23 mg of potassium acetate, 3.1 mg of triphenylphosphine and 2.7 mg of palladium acetate were added to the reaction mixture and stirred at 70° C. for 3 hours after stirred at room temperature for 9 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; toluene] to obtain 94 mg of tert-butyl 2-(benzamido)-4-(2-cyclopenten-1-yl)benzoate as white solid.

Workup

  1. stirringstirred at 70° C. for 3 hours
  2. stirringafter stirred at room temperature for 9 hours
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with 10% citric acid aqueous solution
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified with silica gel column chromatography [eluent; toluene]

Sources & evidence

ORD record
ord-0237828e91794df7b2ef7c1ea4e1fbb7
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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