HCID 14953103, compound → HCID 14953107, compound

HRID 1493329Notes

Reaction equation

HRID 1493329 reaction equation
C[O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:17][C:18]([CH3:24])([CH3:23])[CH2:19][C:20]([OH:22])=[O:21])=[CH:5][CH:4]=1>C(O)(=O)C.Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:17][C:18]([CH3:23])([CH3:24])[CH2:19][C:20]([OH:22])=[O:21])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 14953103HCID 14953103, compound

Product 1

HCID 14953107HCID 14953107, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

2.7 g of 4-[1-(4-methoxybenzyl)benzimidazol-2-yl]-3,3-dimethylbutanoic acid, prepared in Example 68, are dissolved in 40 ml of acetic acid and 40 ml of 48% hydrobromic acid. The mixture is refluxed for 3 hours and the solvents are evaporated off under vacuum. The residue is taken up with a 1N solution of sodium hydroxide so as to adjust the pH to 9-10, and the resulting aqueous phase is washed with ether and then acidified with sulfur dioxide to pH 5.5. The crystals obtained are filtered off, washed with water and then with ether and then chromatographed on silica gel in a 9:1 chloroform/methanol eluent to give 0.4 g of 4-[1-(4-hydroxybenzyl)benzimidazol-2-yl]-3,3-dimethylbutanoic acid in the form of crystals melting at 215°-216° C.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customthe solvents are evaporated off under vacuum
  3. washthe resulting aqueous phase is washed with ether
  4. customThe crystals obtained
  5. filtrationare filtered off
  6. washwashed with water
  7. customwith ether and then chromatographed on silica gel in a 9:1 chloroform/methanol eluent

Sources & evidence

ORD record
ord-57ab5512cd684630a91b2a36f1f3ae57
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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