Sodium Hydroxide → HCID 178440084, compound

HRID 265036Notes

Reaction equation

HRID 265036 reaction equation
[OH-].[Na+].Cl.[OH:4][C:5]([C:8]1[N:9]=[C:10]([CH2:36][CH2:37][CH3:38])[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:12]=1[C:13]([O:15]CC)=[O:14])([CH3:7])[CH3:6]>CO>[OH:4][C:5]([C:8]1[N:9]=[C:10]([CH2:36][CH2:37][CH3:38])[N:11]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:23][CH:24]=2)[C:12]=1[C:13]([OH:15])=[O:14])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178440078HCID 178440078, compound

Product 1

HCID 178440084HCID 178440084, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.65 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 0.31 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{4-[2-(tetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate hydrochloride [prepared as described in Example 18(b)] in 6 ml of methanol, and the resulting mixture was allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to remove the methanol. The concentrate was diluted with water and its pH was adjusted to a value of 3 by the addition of dilute hydrochloric acid, after which it was extracted with ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The resulting residue was triturated with diisopropyl ether, to give 0.15 g of the title compound, melting at 166°-169° C.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customto remove the methanol
  3. additionThe concentrate was diluted with water and its pH
  4. additionwas adjusted to a value of 3 by the addition of dilute hydrochloric acid
  5. extractionafter which it was extracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe resulting residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-c7fdd06d56fa40fdac911f2909aab38a
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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