Citric Acid → AM-206 free acid

HRID 554625Notes

Reaction equation

HRID 554625 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[CH2:21][N:22]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:23][CH3:24])[CH:10]=1.O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[CH2:28]([O:27][C:25]([N:22]([CH2:21][C:12]1[CH:13]=[C:14]([C:17]([F:18])([F:19])[F:20])[CH:15]=[CH:16][C:11]=1[C:9]1[CH:10]=[C:5]([CH2:4][C:3]([OH:35])=[O:2])[CH:6]=[N:7][CH:8]=1)[CH2:23][CH3:24])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67212363(5-{2-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester

Product 1

HCID 45138625AM-206 free acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(5-{2-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester (0.1 g, 0.2 mmol) in THF (2 mL), MeOH (0.5 mL), and H2O (0.5 mL) was treated with lithium hydroxide (0.03 g) and stirred at room temperature until no starting material was seen by analytical LCMS. The reaction was neutralized with citric acid to pH 4 and extracted with EtOAc, and the combined organic layers were washed with H2O, dried over MgSO4, filtered, and concentrated to give Compound 12.

Workup

  1. extractionextracted with EtOAc
  2. washthe combined organic layers were washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f739288aaab84a01ac16e81a9a2fd7ef
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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