Hydrochloric Acid → 2-Butyl-1-[[2'-(N-pivaloyloxymethyltetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

HRID 653730Notes

Reaction equation

HRID 653730 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]2[C:28]([C:32]([OH:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[C:35]([O-])([O-])=O.[K+].[K+].IC[CH2:43][C:44]([CH3:49])([CH3:48])[C:45]([O-:47])=[O:46].Cl>CN(C=O)C.O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]([CH2:35][O:47][C:45](=[O:46])[C:44]([CH3:49])([CH3:48])[CH3:43])[N:26]=[N:25][N:24]=3)=[CH:15][CH:16]=2)[C:8]2[C:28]([C:32]([OH:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86639330HCID 86639330, compoundHCID 178441468HCID 178441468, compound

Product 1

HCID 197921822-Butyl-1-[[2'-(N-pivaloyloxymethyltetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acidYield 23.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid (0.71 g), K2CO3 (0.21 g) and iodomethylpivalate (0.36 g) in DMF (2 ml) was stirred at room temperature for 17 hours. The reaction mixture was digested with water and made acidic (pH 3-4) with 1N-HCl. The mixture was extracted with ethyl acetate and the organic layer was washed with H2O, dried and evaporated to dryness to give a residue. The residue was purified by column chromatography on silica gel to afford colorless powder (0.2 g, 23%), m.p. 188°-191° C.(d).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with H2O
  3. customdried
  4. customevaporated to dryness
  5. customto give a residue
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7592703054434a62ad085ec1474246ca
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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