Tetrahydrofuran → Methyl 4'-[(2-butyl-3H-thieno-(2,3-d)-imidazol-3-yl)-methyl]-(1,1'-biphenyl)-2-carboxylate

HRID 129859ノート

反応式

HRID 129859 の反応式
[CH2:1]([C:5]1[NH:6][C:7]2[CH:12]=[CH:11][S:10][C:8]=2[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[H][H].BrC[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]=1[C:31]([O:33][CH3:34])=[O:32].O1CCC[CH2:36]1>>[CH2:1]([C:5]1[N:9]([CH2:36][C:28]2[CH:27]=[CH:26][C:25]([C:21]3[C:20]([C:31]([O:33][CH3:34])=[O:32])=[CH:19][CH:24]=[CH:23][CH:22]=3)=[CH:30][CH:29]=2)[C:8]2[S:10][CH:11]=[CH:12][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 5

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 193706332-Butyl-thieno-(2,3-d)-imidazoleHCID 19608489Methyl bromomethyl-(1,1'-biphenyl)-2-carboxylateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 19370646Methyl 4'-[(2-butyl-3H-thieno-(2,3-d)-imidazol-3-yl)-methyl]-(1,1'-biphenyl)-2-carboxylate

実験手順

360 mg of the product of step E of Examples 29 and 30 were dissolved at ambient temperature in 7 ml of tetrahydrofuran and 96 mg of sodium hydride at 50% in oil were added in two lots at ambient temperature. After hydrogen had been released, the mixture was stirred for 10 minutes under nitrogen. Then, 610 mg of methyl bromomethyl-(1,1'-biphenyl-)-2-carboxylate (prepared according to EP 0,253,310) were added and the mixture was stirred at ambient temperature for 35 minutes. Then the solvent was evaporated off under nitrogen and 20 ml of water were added. Extraction was carried out with methylene chloride and the extracts were washed with water. The organic phase was dried, filtered and evaporated and the residue was chromatographed on silica (eluant: ethyl acetate 50-cyclohexane 50) to obtain 600 mg of isomer A (Rf=0.40) and 250 mg of isomer B (Rf=0.28).

後処理

  1. stirringthe mixture was stirred at ambient temperature for 35 minutes
  2. customThen the solvent was evaporated off under nitrogen
  3. addition20 ml of water were added
  4. extractionExtraction
  5. washthe extracts were washed with water
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue was chromatographed on silica (eluant: ethyl acetate 50-cyclohexane 50)
  10. customto obtain 600 mg of isomer A (Rf=0.40) and 250 mg of isomer B (Rf=0.28)

出典と根拠

ORDレコード
ord-4f020ab82bcf45e98c6091034bdc2ed7
出典データセット
uspto-grants-1995_11
特許番号
US05470867

反応ノート

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