Water → pivaloyloxymethyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate

HRID 725167

반응식

HRID 725167 반응식
[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]2[C:46]([C:50]([OH:52])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:59]([O:65][CH2:66]I)(=[O:64])[C:60]([CH3:63])([CH3:62])[CH3:61].O>CN(C=O)C>[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:14][CH:15]=2)[C:7]2[C:46]([C:50]([O:52][CH2:66][O:65][C:59](=[O:64])[C:60]([CH3:63])([CH3:62])[CH3:61])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 104401Iodomethyl pivalateHCID 103125632-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid

생성물 1

HCID 178467381pivaloyloxymethyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid (2.2 g) in DMF (10 ml) were added potassium carbonate (0.53 g) and pivaloyloxymethyl iodide (0.94 g), and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. After removal of the solvent, the residue was dissolved in methanol (30 ml) and 1N-HCl (6 ml). The mixture was stirred for one hour at room temperature. The reaction mixture was concentrated to dryness and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and dried. After removal of the solvent, the residue was purified by column chromatography on silica gel to give crystals. The crystals were recrystallized from ethyl acetate-hexane to give colorless crystals (1.13 g. 63%), m.p. 104°-106° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customAfter removal of the solvent
  5. dissolutionthe residue was dissolved in methanol (30 ml)
  6. stirringThe mixture was stirred for one hour at room temperature
  7. concentrationThe reaction mixture was concentrated to dryness
  8. customthe residue was partitioned between water and ethyl acetate
  9. washThe organic layer was washed with water
  10. customdried
  11. customAfter removal of the solvent
  12. customthe residue was purified by column chromatography on silica gel
  13. customto give crystals
  14. customThe crystals were recrystallized from ethyl acetate-hexane
  15. customto give colorless crystals (1.13 g. 63%), m.p. 104°-106° C.

출처 및 근거

ORD 기록
ord-3c18810afaeb45909293c3dc826b651f
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705517

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