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

HRID 921498Notes

Reaction equation

HRID 921498 reaction equation
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.CCCCCC>[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]

Participants

6

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

(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 hexane was added, stirred, filtered and dried to yield (S)-3-(tert-butyl dimethylsilyloxy)glutaric acid monoamide.

Workup

  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

Sources & evidence

ORD record
ord-b2162457c3284c64a7d6ba2b53951e47
Source dataset
uspto-grants-2016_03
Patent number
US09273333B2

Reaction notes

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