Acetic Acid → (S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic Acid

HRID 902616Notes

Reaction equation

HRID 902616 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:27]=2[Cl:36])[CH2:16][C@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH:6]=1.[Li+].[OH-].C(O)(=O)C.C(OCC)(=O)C>C1COCC1.O>[Cl:36][C:27]1[C:28]([C:32]([F:33])([F:34])[F:35])=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:15]([CH2:16][C@H:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:18])[CH2:14][CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:37])=[O:2])[CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium Hydroxide2×HCID 8857Ethyl AcetateHCID 68816647(S)-(3-{3-[[2-Chloro3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid methyl ester

Product 1

HCID 10289391(S)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic AcidYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-(3-{3-[[2-chloro-3-(trifluoromethyl)benzyl](2-phenyl-propyl)amino]propoxy}-phenyl)acetic acid methyl ester (0.6 g, 1.1 mmol) in THF (9 ml) and water (6 ml) was treated with aqueous LiOH (1.0 N, 1.0 ml, 1.0 mmol). After stirring at RT for 2 h, additional LiOH (1.0 ml, 11.0 mmol) was added and stirring was continued for 2 h. The reaction was neutralized with acetic acid and poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude mixture was purified by HPLC to give the title compound as an oil (0.4 g, 75%). MS (ESI) 520.2 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by HPLC

Sources & evidence

ORD record
ord-02e6ba1bf4dc431c9d683e1321be788c
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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