Potassium Carbonate → (S)-(3-{3-[[2-Chloro3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid methyl ester

HRID 902615Notes

Reaction equation

HRID 902615 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14]Br)[CH:6]=1.[Cl:17][C:18]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][C:19]=1[CH2:20][NH:21][CH2:22][C@H:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:21]([CH2:20][C:19]2[CH:31]=[CH:32][CH:33]=[C:34]([C:35]([F:36])([F:37])[F:38])[C:18]=2[Cl:17])[CH2:22][C@H:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:24])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10565189Methyl [3-(3-bromopropoxy)phenyl]acetateHCID 68817028(S)-(2-Chloro-3-trifluoromethyl-benzyl)(2-phenyl-propyl)-amine

Product 1

HCID 68816647(S)-(3-{3-[[2-Chloro3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid methyl esterYield 74.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3-{3-bromo-propoxy}-phenyl)acetic acid methyl ester (0.55 g, 1.5 mmol) and (S)-(2-Chloro-3-trifluoromethyl-benzyl)-(2-phenyl-propyl)-amine (0.55 g, 1.6 mmol) in acetonitrile (10 ml) was treated with solid potassium carbonate(0.4 g, 2.4 mmol). The reaction was heated to reflux and stirred for 48 h. Upon cooling to RT, the reaction was filtered through a pad of celite, washed with ethyl acetate, and the filtrate was concentrated in vacuo. The crude product was purified by column chromatograph (Ethyl acetate:Hexane/20:80) to give the title compound as an oil (0.6 g, 67%). MS (ESI) 534.6 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. filtrationthe reaction was filtered through a pad of celite
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude product was purified by column chromatograph (Ethyl acetate:Hexane/20:80)

Sources & evidence

ORD record
ord-a29a58c4f6fe4744b1a51861f3e22709
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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