Potassium trimethylsilanolate → HCID 178440179, compound

HRID 248642Notes

Reaction equation

HRID 248642 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([CH2:37][CH2:38][CH3:39])[N:11]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]4[NH:36][N:35]=[N:34][N:33]=4)=[CH:22][CH:21]=3)[C:12]=2/[CH:13]=[CH:14]/[C:15]([O:17]C)=[O:16])[C:4]([CH3:7])=[CH:5][CH:6]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH3:1][C:2]1[N:3]([C:8]2[N:9]=[C:10]([CH2:37][CH2:38][CH3:39])[N:11]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]4[NH:33][N:34]=[N:35][N:36]=4)=[CH:22][CH:21]=3)[C:12]=2/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 178440177HCID 178440177, compound

Product 1

HCID 178440179HCID 178440179, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propyl-1-[[2'-(1H-tetrazol-5-yl) 1,1'-biphenyl-4-yl]methyl]-1H-imidazol-5-yl]-2-propenoate (Example 52, 1.55 g, 3 mmol), and potassium trimethylsilanolate (0.96 g, 7.5 mmol) in dry THF (80 mL) was stirred at room temperature for 3 hours under an atmosphere of dry nitrogen. The resulting precipitate was collected by filtration, air dried, and then dissolved in water (50 mL). The free acid was precipitated out by the addition of 1N HCl and collected by filtration giving (E)-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-2-propyl-1-[[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl]-1H-imidazol-5-yl]-2-propenoic acid (1.3 g, 83%) as a partial hydrate, mp 144 150° C.

Workup

  1. filtrationThe resulting precipitate was collected by filtration, air
  2. customdried
  3. dissolutiondissolved in water (50 mL)
  4. customThe free acid was precipitated out by the addition of 1N HCl
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e8870655f5c9423d9698f76cb292cd21
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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