Ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate → HCID 178440150, compound

HRID 52906Notes

Reaction equation

HRID 52906 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:50][CH2:51][CH3:52])[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)(=O)C>[OH:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:50][CH2:51][CH3:52])[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 1

HCID 19036205Ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Product 1

HCID 178440150HCID 178440150, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.28 g of ethyl 4-hydroxymethyl-2-propyl-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (b) above] in 4 ml of 75% v/v aqueous acetic acid was stirred at 60° C. for 2 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was dissolved in toluene. The resulting solution was again concentrated by evaporation under reduced pressure, to remove as much water and acetic acid as possible. The residue was then purified by column chromatography through silica gel, using 9:1 and 4:1 by volume mixtures of methylene chloride and methanol as the eluent, to give 0.20 g of the title compound as an amorphous solid.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. dissolutionthe residue was dissolved in toluene
  3. concentrationThe resulting solution was again concentrated by evaporation under reduced pressure
  4. customto remove as much water and acetic acid as possible
  5. customThe residue was then purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-dea9f34729ea4632933ce4e1c591d768
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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