Potassium trimethylsilanolate → HCID 178425432, compound

HRID 248639Notes

Reaction equation

HRID 248639 reaction equation
[CH:1]1([C:4]2[N:5]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:6]([C:16]([O:18]C)=[O:17])=[C:7]([N:9]3[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]3[CH3:15])[N:8]=2)[CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH:1]1([C:4]2[N:5]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]4[NH:37][N:36]=[N:35][N:34]=4)=[CH:23][CH:22]=3)[C:6]([C:16]([OH:18])=[O:17])=[C:7]([N:9]3[C:10]([CH3:15])=[CH:11][CH:12]=[C:13]3[CH3:14])[N:8]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 178498704HCID 178498704, compound

Product 1

HCID 178425432HCID 178425432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-cyclopropyl-4-(2,5 dimethyl-1H-pyrrol-1-yl)-1 [(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylate (Example 42, 1.91 g) in anhydrous THF was added potassium trimethylsilanolate (1.57 g) and the mixture stirred at ambient temperature for 20 hours. The solvent was removed under reduced pressure and the residue taken up in water (25 mL). The aqueous solution was filtered and extracted with ethyl acetate. The aqueous layer was acidified to pH 4.5 with 1N HCl and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and evaporated to give the title compound 2-cyclopropyl-4-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole-5-carboxylic acid. MS (CI, CH4 +NH3) 480 (M+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe aqueous solution was filtered
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-59e7f51c7dbf4a9b99381618ac1e52ec
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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