Acetic acid, 2-(4-formylphenoxy)- → 2-(4-Carboxymethoxy-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic Acid Ethyl Ester

HRID 2117001Notes

Reaction equation

HRID 2117001 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1C1(N)CCCCC1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:20]([C:22]1[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:23]=1)=O.OOS([O-])=O.[K+]>CN(C=O)C.O>[CH2:8]([O:7][C:5]([C:4]1[CH:10]=[CH:11][C:12]2[N:1]([CH:2]3[CH2:3][CH2:4][CH2:10][CH2:11][CH2:12]3)[C:20]([C:22]3[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][CH:23]=3)=[N:1][C:2]=2[CH:3]=1)=[O:6])[CH3:9]

Participants

6

Reactant 3

HCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 22669240Ethyl 3-amino-4-(aminocyclohexyl)benzoateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 233782182-(4-Carboxymethoxy-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic Acid Ethyl EsterYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of example 1, ethyl 3-amino-4-(aminocyclohexyl)benzoate (1.077 g, 4.1 mmol) and 4-formylphenoxyacetic acid (0.748 g, 4.15 mmol) were dissolved in a mixture of DMF (8 mL) and water (0.5 mL). Oxone® (0.7 equivalent, 2.87 mmol, 1.764 g) was added and the mixture stirred for 30 min at room temperature (HPLC complete). Water was added to precipitate the product, which was collected by filtration, washed with water and dried (1.130 g, 65% yield, brown solid).

Workup

  1. customto precipitate the product, which
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried (1.130 g, 65% yield, brown solid)

Sources & evidence

ORD record
ord-053d28933ccf4cf4b027c9d8dd881abe
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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