反応 #41551

ord-50ff626390254e4b8c9004508484924c

反応方程式

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

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07728025B2uspto-grants-2010_06