반응 #41551

ord-50ff626390254e4b8c9004508484924c

반응 방정식

O=C([O-])O.[Na+]
sodium bicarbonate
CC(C)NC(C)C
diisopropylamine
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenyl phosphine
OCCc1ccccc1
2-phenyl-ethanol
CC(=O)N1CCCC1c1cc2c(cc1O)nc(-c1ccccn1)n2COCC[Si](C)(C)C
1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone
CC(=O)N1CCCC1c1cc2c(cc1O)nc(-c1ccccn1)n2COCC[Si](C)(C)C
1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone
CC(C)NC(C)C
diisopropylamine
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenyl phosphine
OCCc1ccccc1
2-phenyl-ethanol
CC(=O)N1CCCC1c1cc2c(cc1OCCc1ccccc1)nc(-c1ccccn1)n2COCC[Si](C)(C)C
1-(2-(6-phenethyloxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타the reaction liquid
  2. 2
    기타the reaction liquid
  3. 3
    workup.STIRRINGwas stirred overnight at room temperature
  4. 4
    추출this was extracted with ethyl acetate
  5. 5
    건조dried with anhydrous magnesium sulfate
  6. 6
    기타The solvent was evaporated away under reduced pressure
  7. 7
    기타the resulting residue was purified
  8. 8
    기타through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate)
  9. 9
    기타to obtain the entitled compound as a brown oily substance

실험 절차

0.019 ml of diisopropylamine, 27.6 mg of triphenyl phosphine and 0.011 ml of 2-phenyl-ethanol were added in order to a tetrahydrofuran (1 ml) solution of 29.2 mg of 1-(2-(6-hydroxy-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)pyrrolidin-1-yl)-ethanone obtained in Example 121 (step 10), and the reaction liquid was stirred for 6 hours at room temperature. 0.040 ml of diisopropylamine, 53.2 mg of triphenyl phosphine and 0.023 ml of 2-phenyl-ethanol were added in order to the reaction liquid, and the reaction liquid was stirred overnight at room temperature. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and this was extracted with ethyl acetate, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), ethyl acetate) to obtain the entitled compound as a brown oily substance.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07728025B2uspto-grants-2010_06