Methanol → Methyl (3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-phenyl)acetate

HRID 902628Notes

Reaction equation

HRID 902628 reaction equation
Cl.[Cl:2][C:3]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][C:4]=1[CH2:5][N:6]([CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18]([OH:20])=[O:19])[CH:14]=[CH:15][CH:16]=1.[CH3:43]O>S(=O)(=O)(O)O>[CH3:43][O:19][C:18](=[O:20])[CH2:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:6]([CH2:5][C:4]2[CH:35]=[CH:36][CH:37]=[C:38]([C:39]([F:40])([F:41])[F:42])[C:3]=2[Cl:2])[CH2:21][CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 16078973GW3965 hydrochloride

Product 1

HCID 10188816Methyl (3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2,2-diphenylethyl)amino]propoxy}-phenyl)acetateYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of (3-{3[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetic acid hydrochloride salt (Example 1d, 0.1 g, 0.2 mmol) in methanol (2 ml) was added concentrated sulfuric acid (2 drops). After the resulting mixture was heated to reflux for 2 h solvent was removed under vacuum. The residue was dissolved in water and neutralized to pH=7. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with, brine, dried over magnesium sulfate, and concentrated in vacco to give 900 mg (93%) of the title compound as an oil. MS m/e 596.2 (M+H)+.

Workup

  1. temperatureAfter the resulting mixture was heated
  2. temperatureto reflux for 2 h solvent
  3. customwas removed under vacuum
  4. dissolutionThe residue was dissolved in water and neutralized to pH=7
  5. extractionThe aqueous layer was extracted with ethyl acetate three times
  6. washThe combined organic layers were washed with, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacco

Sources & evidence

ORD record
ord-6c1a046fbca34dc895e68a18ddff86ae
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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