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

HRID 129859노트

반응식

HRID 129859 반응식
[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]

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4f020ab82bcf45e98c6091034bdc2ed7
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470867

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