Sodium Hydroxide → HCID 178441913, compound

HRID 36176Notes

Reaction equation

HRID 36176 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:7](=[O:21])[N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([O:19]C)=[O:18])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:35]3[NH:39][N:38]=[N:37][N:36]=3)=[CH:25][CH:24]=2)[C:7](=[O:21])[N:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([OH:19])=[O:18])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178441912HCID 178441912, compound

Product 1

HCID 178441913HCID 178441913, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 mg (0.038 mmole) of 5-n-butyl-2-[2-(carbomethoxy)benzyl]-2,4-dihydro-4-[[2'-(5-tetrazolyl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol- 3-one (from Example 6) in 200 μl of dry THF was added all at once 84 μl (0.084 mmole) of 1N sodium hydroxide in methanol. The mixture was stirred overnight at room temperature and then evaporated to dryness. The residual solid was dissolved in 1.5 ml of methanol and treated with 90 μl of 1N HCl in methanol (final pH 2). The solvent was evaporated, and the residue was leached with CHCl3. After removal of insoluble solid (NaCl) by filtration through glass wool, the filtrate was concentrated in vacuo and then re-concentrated from toluene. The residue was dried overnight in the presence of P2O5 to give 20 mg (95%) of the titled compound as a stiff, white foam, mp>106° C. (gradual), homogeneous by TLC in 90:10:0.1 CH2Cl2 --MeOH--AcOH; mass spectrum (FAB) m/e 510 (M+1)+.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residual solid was dissolved in 1.5 ml of methanol
  3. additiontreated with 90 μl of 1N HCl in methanol (final pH 2)
  4. customThe solvent was evaporated
  5. customAfter removal of insoluble solid (NaCl)
  6. filtrationby filtration through glass wool
  7. concentrationthe filtrate was concentrated in vacuo
  8. concentrationre-concentrated from toluene
  9. dry with materialThe residue was dried overnight in the presence of P2O5

Sources & evidence

ORD record
ord-3c52c6a051eb42bca17c3589722fd1b5
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Reaction notes

Loading…