2-Mercaptoethanol → tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate

HRID 1260113노트

반응식

HRID 1260113 반응식
[N:1]1([C:7]([C@@H:9]2[CH2:14][C@H:13]([N:15](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH2:16][CH2:17][CH3:18])[CH2:12][N:11]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.[OH-].[Li+].C(O)CS>CN(C=O)C.C(=O)(O)[O-].[Na+]>[N:1]1([C:7]([C@@H:9]2[CH2:14][C@H:13]([NH:15][CH2:16][CH2:17][CH3:18])[CH2:12][N:11]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 15672-MercaptoethanolHCID 168937Lithium hydroxide, monohydrateHCID 58355213tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-{[(2-nitrophenyl)sulfonyl](propyl)amino}piperidine-1-carboxylate

생성물 1

HCID 58355640tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate수율 71.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

tert-Butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-{[(2-nitrophenyl)sulfonyl](propyl)amino}piperidine-1-carboxylate (4.02 g) and lithium hydroxide monohydrate (1.56 g) were dissolved in DMF (20 ml), thioglycol acid (1.3 ml) was added at room temperature, and the mixture was stirred for 2 days at room temperature. The reaction mixture 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 magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:9-10:0) was concentrated under reduced pressure. The residue was diluted with 10% aqueous citric acid solution, and washed with ethyl acetate. The aqueous layer was neutralized with aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (1.89 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (1:9-10:0)
  6. concentrationwas concentrated under reduced pressure
  7. additionThe residue was diluted with 10% aqueous citric acid solution
  8. washwashed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-6fe950ff2fae4373b02e0918c26e531a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466282B2

반응 노트

불러오는 중…