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

HRID 921497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921497
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]

Komponenten

6

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8003PentaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e06f9eed347748b8b707ff483f375a7b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273333B2

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