2,3-Difluorophenylacetic acid → HCID 178520265, compound

HRID 1375649Notes

Reaction equation

HRID 1375649 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:11]([N:13]2[CH2:17][CH:16]=[CH:15][CH2:14]2)=[O:12])[NH:9][CH:10]=1)=[O:5])C.[F:18][C:19]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:26]C(O)=O>C1COCC1>[F:18][C:19]1[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:26][C:4]([C:6]1[N:7]=[C:8]([C:11]([N:13]2[CH2:14][CH:15]=[CH:16][CH2:17]2)=[O:12])[NH:9][CH:10]=1)=[O:5]

Participants

4

Reactant 2

HCID 5207722,3-Difluorophenylacetic acidHCID 178469896HCID 178469896, compound

Product 1

HCID 178520265HCID 178520265, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-(2,5-dihydro-pyrrole-1-carbonyl)-1H-imidazole-4-carboxylic acid ethyl ester (100 mg, 0.43 mmol) and (2,3-difluoro-phenyl)acetic acid (75 mg, 0.44 mmol) in anhydrous THF (5 mL) was added LDMS (1.0M in THF, 1.5 mL, 1.5 mmol) at −78° C. After addition of LDMS, the dry-ice bath was removed and the reaction was stirred at ambient temperature for 6 hours. To this reaction mixture was added 1 mL of sat. NH4Cl solution and EtOAc then the organic layer was separated and dried over MgSO4. After removal of solvent, the residue was washed with water to afford the title compound as a yellow solid. This crude product was used directly for the next step without further purification. MS (ES+): m/e=318.2 (M+H); Rt=3.21 minutes.

Workup

  1. additionAfter addition of LDMS
  2. customthe dry-ice bath was removed
  3. additionTo this reaction mixture was added 1 mL of sat. NH4Cl solution and EtOAc
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. customAfter removal of solvent
  7. washthe residue was washed with water

Sources & evidence

ORD record
ord-9233b5ad024a45e18e2b525ab9d01904
Source dataset
uspto-grants-2007_01
Patent number
US07169800B2

Reaction notes

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