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

HRID 1007692Notes

Reaction equation

HRID 1007692 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-1d0c45db79c046e5ab043e99e97b862e
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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