Sodium Methoxide → HCID 178508316, compound

HRID 278489Notes

Reaction equation

HRID 278489 reaction equation
C[O-].[Na+].[C:4]([NH:7][NH2:8])([NH2:6])=[NH:5].Cl.[Si]([O:17][CH2:18][C@@H:19]([N:28]1[CH:32]=[C:31]([C:33](OC)=O)[N:30]=[CH:29]1)[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(C(C)(C)C)(C)C>CO>[NH2:5][C:4]1[NH:7][N:8]=[C:33]([C:31]2[N:30]=[CH:29][N:28]([C@@H:19]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:18][OH:17])[CH:32]=2)[N:6]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 53683119methyl (S)-1-[1-(tert-butyldimethylsilyloxy)-4-phenyl-2-butyl]imidazole-4-carboxylateHCID 178418668HCID 178418668, compound

Product 1

HCID 178508316HCID 178508316, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 28% NaOMe in methanol (772 mg) was added to an ice cooled solution of aminoguanidine hydrochloride (332 mg) in methanol (5 ml). After 10 minutes, methyl (S)-1-[1-(tert-butyldimethylsilyloxy)-4-phenyl-2-butyl]-imidazole-4-carboxylate (obtained in Example 6) (389 mg) in methanol (2 ml) was added to the mixture and the resulting mixture was stirred at reflux for 22 hours. After cooling, the insoluble material was removed and then the filtrate was evaporated. The residue was diluted with water and the solution was acidified to pH 4 with 6N HClaq. The resulting mixture was washed with CHCl3. The aqueous layer was purified by HP-20 (50 cc) column chromatography eluting with water/2-propanol (9:1) and lyophilized to give (S)-2-[4-(5-amino-1,2,4-triazol-3-yl)-1-imidazolyl]-4-phenylbutan-1-ol (107 mg).

Workup

  1. temperatureat reflux for 22 hours
  2. temperatureAfter cooling
  3. customthe insoluble material was removed
  4. customthe filtrate was evaporated
  5. additionThe residue was diluted with water
  6. washThe resulting mixture was washed with CHCl3
  7. customThe aqueous layer was purified by HP-20 (50 cc) column chromatography
  8. washeluting with water/2-propanol (9:1)

Sources & evidence

ORD record
ord-b08f1c13906343298305cd53151af055
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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