Dichloromethane → HCID 67320226, 화합물

HRID 1260009

반응식

HRID 1260009 반응식
C([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([N:17]([CH2:39][CH:40]([CH3:42])[CH3:41])[C@H:18]1[CH2:23][C@@H:22]([C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:25])[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]1)=[O:16])=C.C([Zn]CC)C.CCC[CH2:51][CH2:52][CH3:53].ICI.[Cl:57]CCl>Cl>[ClH:57].[ClH:57].[CH:51]1([O:3][CH2:4][CH2:5][N:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=[C:7]2[C:15]([N:17]([CH2:39][CH:40]([CH3:41])[CH3:42])[C@H:18]2[CH2:23][C@@H:22]([C:24]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[O:25])[CH2:21][NH:20][CH2:19]2)=[O:16])[CH2:52][CH2:53]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6346DiiodomethaneHCID 58355228HCID 58355228, 화합물HCID 178443585HCID 178443585, 화합물

생성물 1

HCID 67320226HCID 67320226, 화합물

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

To a solution of tert-butyl (3S,5R)-3-[({1-[2-(ethenyloxy)ethyl]-1H-benzimidazol-2-yl}carbonyl)(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (323 mg) and 1M diethylzinc-hexane solution (2.5 ml) in dichloromethane (5 ml) was added dropwise diiodomethane (443 μl) at room temperature over 5 min, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in methanol (5 ml), 4M hydrogen chloride-ethyl acetate (5 ml) was added and the mixture was stirred at room temperature for 5 hr. The reaction mixture was concentrated, and the residue was subjected to reversed-phase preparative HPLC and the eluted fraction was concentrated under reduced pressure. The residue was diluted with aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. 4M Hydrogen chloride-ethyl acetate (1 ml) was added and the mixture was stirred for 5 min. The solvent was evaporated under reduced pressure to give the object product (35 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (5 ml)
  6. addition4M hydrogen chloride-ethyl acetate (5 ml) was added
  7. stirringthe mixture was stirred at room temperature for 5 hr
  8. concentrationThe reaction mixture was concentrated
  9. concentrationthe eluted fraction was concentrated under reduced pressure
  10. additionThe residue was diluted with aqueous sodium bicarbonate
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe extract was washed with saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. addition4M Hydrogen chloride-ethyl acetate (1 ml) was added
  15. stirringthe mixture was stirred for 5 min
  16. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-ed40d459618f4143b67f0e7137776569
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466282B2

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