Acetic Acid → HCID 178467659, compound

HRID 265132Notes

Reaction equation

HRID 265132 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])[N:9]=1)[CH3:2].C(O)(=O)C.C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[NH:36][N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:10]([OH:13])([CH3:11])[CH3:12])[N:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6457TriphenylcarbinolHCID 19036157Ethyl 2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Product 1

HCID 178467659HCID 178467659, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 600 mg of ethyl 2-ethoxymethyl -4-(1-hydroxy-1-methylethyl)-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 hours. 10 ml of water were then added, and the mixture was then 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 400 mg of the title compound in an amorphous powder.

Workup

  1. temperaturethe mixture was then 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 toluene

Sources & evidence

ORD record
ord-9d4e72a29f0f4f20b71c9ec984cf7dd9
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

Loading…