Hydrochloric Acid → (3-{4-[(2-Chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic Acid

HRID 902625Notes

Reaction equation

HRID 902625 reaction equation
C[O:2][C:3](=[O:42])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:32]=2[Cl:41])[CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=1.[OH-].[Na+].Cl>CO.O>[Cl:41][C:32]1[C:33]([C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:15]([CH2:16][CH:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:42])=[O:2])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69254114(3-{4-[(2-Chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic acid methyl ester

Product 1

HCID 59701454(3-{4-[(2-Chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic AcidYield 65.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of (3-{4-[(2-chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic acid methyl ester (29 mg, 0.05 mmol) and NaOH (126 mg, 3.15 mmol) in MeOH (3 ml) and water (1 ml) was heated to 50° for 30 minutes. The reaction was cooled, neutralized with aqueous HCl (3.15 mmol), diluted with water and extracted with ethyl acetate. The extracts were dried and the solvent evaporated. Trituration of the residue with cyclohexane gave the title compound as a white powder (19 mg, 65%). MS (ESI) 580.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. customThe extracts were dried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-a5cd3a964b81430389e3a24a19ae141a
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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