Water → HCID 178441663, compound

HRID 653889Notes

Reaction equation

HRID 653889 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:7]([CH2:14][OH:15])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Na+]>Cl.O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[NH:33][N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:7]([CH2:14][OH:15])=[C:8]([C:10]([F:12])([F:11])[F:13])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19815344HCID 19815344, compound

Product 1

HCID 178441663HCID 178441663, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.06 g of 2-butyl-5-hydroxymethyl-4-trifluoromethyl-1-[(2'-(triphenylmethyltetrazol-5-yl)biphenyl-4-yl)methyl]imidazole in 40 mL of 10% hydrochloric acid and 80 mL of tetrahydrofuran was stirred at 25° for 2 hours and then poured into water containing an excess of sodium hydroxide. The aqueous solution was washed with diethyl ether, adjusted to pH 3 with 10% hydrochloric acid, and then extracted with chloroform. The combined chloroform extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (elution: 10% methanol/chloroform) furnished 2.04 g of 2-butyl-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-4-trifluoromethylimidazole as an amorphous solid.

Workup

  1. washThe aqueous solution was washed with diethyl ether
  2. extractionextracted with chloroform
  3. washThe combined chloroform extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washColumn chromatography (elution: 10% methanol/chloroform)

Sources & evidence

ORD record
ord-be3798480f854d969da864e062f04e7f
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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