(S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate → (S)-3-[tert-butyldimethylsilyloxy]glutaric acid monoamide

HRID 921497노트

반응식

HRID 921497 반응식
C([O:8][C:9](=[O:24])[CH2:10][C@@H:11]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][C:13]([NH2:15])=[O:14])C1C=CC=CC=1>C(OCC)(=O)C.[Pd].ClCCl.CCCCC>[Si:17]([O:16][C@H:11]([CH2:10][C:9]([OH:24])=[O:8])[CH2:12][C:13]([NH2:15])=[O:14])([C:20]([CH3:22])([CH3:23])[CH3:21])([CH3:19])[CH3:18]

참가 물질

6

반응물 1

HCID 125499654(S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate

생성물 1

HCID 124674414(S)-3-[tert-butyldimethylsilyloxy]glutaric acid monoamide

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 6344Dichloromethane용매HCID 8003Pentane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
5 °C

실험 절차

(S)-Benzyl-3-(tert-butyl dimethylsilyloxy)glutaramate (100 g) was dissolved in ethyl acetate and placed in pressure flask. To this Palladium on charcoal (5%, 1 g) was added and stirred under hydrogen atmosphere (˜2.8 Kg). Palladium was removed by filtration. The filtrate was mixed with water and adjusted pH to ˜9.0 by using Aq ammonia solution. The reaction mass was stirred and layers were separated. The aqueous phase was washed with dichloromethane and dichloromethane was added to aqueous phase. The reaction mass was cooled to 5° C. and pH was adjusted to 4.0 with Aq phosphoric acid. The reaction mass was stirred and layers were separated. The organic phase was washed with water and dried over sodium sulphate. The organic layer was evaporated under vacuum to yield residue. Residue was dissolved in dichloromethane and to this solution pentane was added, stirred, filtered and dried to yield (S)-3-(tert-butyl dimethylsilyloxy)glutaric acid monoamide.

후처리

  1. customplaced in pressure flask
  2. customPalladium was removed by filtration
  3. additionThe filtrate was mixed with water and adjusted pH to ˜9.0
  4. stirringThe reaction mass was stirred
  5. customlayers were separated
  6. washThe aqueous phase was washed with dichloromethane and dichloromethane
  7. additionwas added to aqueous phase
  8. stirringThe reaction mass was stirred
  9. customlayers were separated
  10. washThe organic phase was washed with water
  11. dry with materialdried over sodium sulphate
  12. customThe organic layer was evaporated under vacuum
  13. customto yield residue
  14. additionwas added
  15. stirringstirred
  16. filtrationfiltered
  17. customdried

출처 및 근거

ORD 기록
ord-e06f9eed347748b8b707ff483f375a7b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273333B2

반응 노트

불러오는 중…