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

HRID 265138Notes

Reaction equation

HRID 265138 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:53][O:54][CH:55]([CH3:57])[CH3:56])[N:8]([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:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[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]([CH2:53][O:54][CH:55]([CH3:57])[CH3:56])[N:8]([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:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6457TriphenylcarbinolHCID 19036290Isopropyl 4-(1-hydroxy-1-methylethyl)-2-isopropoxymethyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Product 1

HCID 178459022Isopropyl 4-(1-hydroxy-1-methylethyl)-2-isopropoxymethyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateYield 95.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 609 mg of isopropyl 4-(1-hydroxy-1-methylethyl)-2-isopropoxymethyl-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 2.5 hours. 10 ml of water were then added, after which the mixture was 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 benzene, to give 398 mg of the title compound as an amorphous powder.

Workup

  1. temperatureafter which the mixture was cooled 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 benzene

Sources & evidence

ORD record
ord-d6714f73396b4d64abb3bc70e2cb97ca
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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