HCID 178459023, compound → HCID 178459027, compound

HRID 265136Notes

Reaction equation

HRID 265136 reaction equation
[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:34][O:35][CH2:36][CH2:37][CH3:38])[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]CCC)=[O:11])([CH3:4])[CH3:3]>O.[OH-].[Li+].O1CCOCC1>[OH:1][C:2]([C:5]1[N:6]=[C:7]([CH2:34][O:35][CH2:36][CH2:37][CH3:38])[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]([OH:12])=[O:11])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 178459023HCID 178459023, compound

Product 1

HCID 178459027HCID 178459027, compoundYield 64.9%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 168937Lithium hydroxide, monohydrateSolvent

Procedure

394 mg of propyl 4-(1-hydroxy-1-methylethyl)-2-propoxymethyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in Example 90(b)] were dissolved in a solution of 88 mg of lithium hydroxide monohydrate in 10 ml of a 50% v/v aqueous Solution of dioxane, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction solution was concentrated by distillation under reduced pressure, and the dioxane was removed by distillation under reduced pressure. The concentrate was then cooled with ice, and 2.1 ml of 1N aqueous hydrochloric acid were added. The crystals which precipitated were collected by filtration, to give 235 mg of the title compound, melting at 166°-168° C.

Workup

  1. concentrationAt the end of this time, the reaction solution was concentrated by distillation under reduced pressure
  2. customthe dioxane was removed by distillation under reduced pressure
  3. temperatureThe concentrate was then cooled with ice, and 2.1 ml of 1N aqueous hydrochloric acid
  4. additionwere added
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-ec264271f93a40c2a7330688ef019623
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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