Sodium Hydroxide → HCID 18537537, compound

HRID 412201Notes

Reaction equation

HRID 412201 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[C:14]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:13]=[C:12]1[CH3:30])C.[OH-].[Na+]>CCO.CCOC(C)=O>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:14]2[N:13]=[C:12]([CH3:30])[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:31])=[O:3])[C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 25190480HCID 25190480, compound

Product 1

HCID 18537537HCID 18537537, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Scheme 1, (C)) To a solution of 7-[4,5-Bis-(4-fluoro-phenyl)-2-methyl-imidazol-1-yl]-heptanoic acid ethyl ester (1.9 g, 4.4 mmol) in EtOH (10 mL) was added NaOH (10 N, 2 mL, 20 mmol). The resulting mixture was stirred at rt for 1 hour, diluted with EtOAc (100 mL), washed by HCl (0.5 N), and then was dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: MeOH/CH2Cl2). This compound was obtained as a white solid in HCl salt form (1.9 g, 4.3 mmol, 98% yield): 1H NMR (DMSO): δ1.15 (m, 4H), 1.37 (t, 2H), 1.47 (t, 2H), 2.13 (t, 2H), 2.73 (s, 3H), 4.03 (t, 2H), 7.35 (t,2H), 7.45 (m, 4H), 7.57 (m, 2H), 12.1 (b, 1H).

Workup

  1. washwashed by HCl (0.5 N)
  2. dry with materialwas dried over MgSO4
  3. filtrationAfter filtration and concentration in vacuo
  4. customthe residue was purified by flash chromatography (SiO2: MeOH/CH2Cl2)
  5. customThis compound was obtained as a white solid in HCl salt form (1.9 g, 4.3 mmol, 98% yield)

Sources & evidence

ORD record
ord-35ca726d65a143e8bb4ec3c3a7a6ce93
Source dataset
uspto-grants-2003_05
Patent number
US06562846B2

Reaction notes

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