2-(4-Fluorophenyl)acetic acid → HCID 22643386, compound

HRID 2414812Notes

Reaction equation

HRID 2414812 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](O)=[O:23])=[CH:17][CH:16]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][NH:13][C:22](=[O:23])[CH2:21][C:18]2[CH:19]=[CH:20][C:15]([F:14])=[CH:16][CH:17]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

7

Reactant 4

HCID 98372-(4-Fluorophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 1378573,5-DimethoxyphenethylamineHCID 2724699PyBOP

Product 1

HCID 22643386HCID 22643386, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3,5-dimethoxy-phenyl)-ethylamine (1.01 g, 5.57 mmol) in anhydrous DMF (50 mL) is added 4-fluorophenyl acetic acid (860 mg, 5.57 mmol), PyBOP (3.17 g) and N-ethyldiisopropylamine (2.2 mL, 12.8 mmol). The mixture is stirred at rt for 14 h. Water (60 mL) is added, and the mixture is extracted with EtOAc (4×60 mL). The combined organic phases are washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography (EtOAc/Hex, 7:3) to afford the title compound as a yellow oil.

Workup

  1. extractionthe mixture is extracted with EtOAc (4×60 mL)
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography (EtOAc/Hex, 7:3)

Sources & evidence

ORD record
ord-9c2b20a7d03e419294d671e76a5b09bd
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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