Hydrochloric Acid → 3-(4-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoylamino)-butyric acid

HRID 1669313Notes

Reaction equation

HRID 1669313 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][CH:5]([NH:7][C:8](=[O:39])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:16]([C:23]2[CH:24]=[N:25][C:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=3)=[CH:27][CH:28]=2)[CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:11][CH:10]=1)[CH3:6].[OH-].[Na+].Cl>C1COCC1>[CH3:21][C:19]([CH3:20])([CH3:22])[CH2:18][CH2:17][CH:16]([C:23]1[CH:24]=[N:25][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=2)=[CH:27][CH:28]=1)[O:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH:5]([CH3:6])[CH2:4][C:3]([OH:40])=[O:2])=[O:39])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67343031HCID 67343031, compound

Product 1

HCID 597294063-(4-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoylamino)-butyric acidYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-{4,4-Dimethyl-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-pentyloxy}-benzoylamino)-butyric acid methyl ester are taken into THF (1.0 mL) and treated with NaOH (1.0 mL, 5.0 N), then refluxed under nitrogen. The reaction mixture is neutralized with HCl (1.0 mL, 5.0 N), extracted with ethyl ether, dried over sodium sulfate. Concentration gives the title compound, (163 mg, 0.15 mmol) 72% 2 steps. MS (ES): 541.3 [M+H]−, the structure is also confirmed by proton NMR.

Workup

  1. temperaturerefluxed under nitrogen
  2. extractionextracted with ethyl ether
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-8527f3ef65d7457ebe0a9cc794e3e0ae
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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