Benzyl Bromide → Benzyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

HRID 420642Notes

Reaction equation

HRID 420642 reaction equation
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH2:3][C:4]([O-:6])=[O:5].[Li+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=1)[CH2:3][C:4]([O:6][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:5]

Participants

6

Reactant 2

HCID 7498Benzyl BromideHCID 23693664Lithium 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

Product 1

HCID 59666221Benzyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of lithium 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate (2.0 g, 7.9 mmol) (Example 2A) in water (15 ml) is added a solution of Aliquat 336® (3.1 g) and benzyl bromide (1.35 g, 7.5 mmol) in dichloromethane (15 ml). The reaction mixture is stirred for two days at room temperature, then extracted with dichloromethane (500 ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography over silica gel 60 with cyclohexane/ethyl acetate mixtures as eluent.

Workup

  1. extractionextracted with dichloromethane (500 ml)
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography over silica gel 60 with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-668855b86b7c461f877532ce50aa3ef7
Source dataset
uspto-grants-2012_01
Patent number
US08097629B2

Reaction notes

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