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

HRID 902675Notes

Reaction equation

HRID 902675 reaction equation
[Cl:1][C:2]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]([CH2:20][C@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=1.Cl.[CH3:38]O>>[CH3:38][O:18][C:17](=[O:19])[CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]2[CH:29]=[CH:30][CH:31]=[C:32]([C:33]([F:34])([F:35])[F:36])[C:2]=2[Cl:1])[CH2:20][C@H:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22])[CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10289391(S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic Acid

Product 1

HCID 68816647(S)-(3-{3-[[2-Chloro3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid methyl esterYield 90%

Procedure

To a solution of (3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-((S)-2-phenyl-propyl)-amino]-propoxy}-phenyl)-acetic acid (Example 10, 0.5 g, 3.7 mmol) in methanol (300 ml) was added concentrated hydrochloric acid (10 ml). 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. The combined organic layers were washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, and concentrated in vacco to give the title compound as colorless oil (0.5 g, 90%). MS m/e 534.6 (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
  6. washThe combined organic layers were washed with saturated sodium bicarbonate, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacco

Sources & evidence

ORD record
ord-aa2fefa3d8a74610bc4f7060488a88b4
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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