Potassium trimethylsilanolate → HCID 178440179, compound

HRID 1197601Notes

Reaction equation

HRID 1197601 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-4ba487253287449ab9e8ad7191e9603a
Source dataset
uspto-grants-1994_01
Patent number
US05276048

Reaction notes

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