Acetic Acid → Methyl 4-(1-hydroxy-1-methylethyl)-2-(1-methoxyethyl)-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 53003

Reaction equation

HRID 53003 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH:51]([O:53][CH3:54])[CH3:52])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:9]=1[C:10]([O:12][CH3:13])=[O:11])([CH3:4])[CH3:3].C(O)(=O)C.C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>O>[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH:51]([O:53][CH3:54])[CH3:52])[N:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:9]=1[C:10]([O:12][CH3:13])=[O:11])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6457TriphenylcarbinolHCID 19036227Methyl 4-(1-hydroxy-1-methylethyl)-2-(1-methoxyethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Product 1

HCID 178497993Methyl 4-(1-hydroxy-1-methylethyl)-2-(1-methoxyethyl)-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 600 mg of methyl 4-(1-hydroxy-1-methylethyl)-2-(1-methoxyethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (a) above] in 10 ml of a 25% v/v aqueous solution of acetic acid was stirred at 60° C. for 1.5 hours. The solution was then mixed with 10 ml of water and cooled with ice. The trityl alcohol which appeared as crystals was filtered off. The filtrate was concentrated by distillation under reduced pressure, and then acetic acid and water were distilled off as azeotropic mixtures with toluene, to give 331 mg of the title compound as an amorphous powder.

Workup

  1. temperaturecooled with ice
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated by distillation under reduced pressure
  4. distillationacetic acid and water were distilled off as azeotropic mixtures with toluene

Sources & evidence

ORD record
ord-1636d923a9ea4d7fa86118160a5b2750
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Linked notes

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