Potassium Carbonate → HCID 69798572, compound

HRID 896339Notes

Reaction equation

HRID 896339 reaction equation
C([O:4][CH2:5][C:6]1[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19](C)(C)C)[C:9]2[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:8]=2[N:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.CCOC(C)=O>[C:28]([C:26]1[CH:25]=[CH:24][C:9]2[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:23])[CH3:19])[C:6]([CH2:5][OH:4])=[N:7][C:8]=2[CH:27]=1)#[N:29]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 69708671HCID 69708671, compound

Product 1

HCID 69798572HCID 69798572, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,2-Dimethyl-propionic acid 6-(2-acetoxymethyl-5-cyano-benzoimidazol-1-yl)-hexyl ester (7.2 g, 18 mmol) and K2CO3 (14 g, 101 mmol) in MeOH (100 mL) was stirred at the ambient temperature for 4 h. The nixture was diluted with EtOAc (100 mL) and filtered. The filtrate was evaporated. The residue was dissolved in EtOAc (300 mL) and washed with water and brine. The organic layer was dried over MgSO4 and evaporated. The residue was left for 2 weeks before being purified by flash chromatography (hexanes:acetone 1:1) to give 4.1 g (72%) of acetic acid 6-(5-cyano-2-hydroxymethyl-benzoimidazol-1-yl)-hexyl ester as a white solid.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionThe residue was dissolved in EtOAc (300 mL)
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. waitThe residue was left for 2 weeks
  8. custombefore being purified by flash chromatography (hexanes:acetone 1:1)

Sources & evidence

ORD record
ord-544e3d3f6f8c4892a0ef829448e23772
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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