benzyl O-acetoacetyl-N-trifluoroacetyl-L-serinate → O-acetoacetyl-N-trifloroacetyl-L-serine

HRID 2165229Notes

Reaction equation

HRID 2165229 reaction equation
[C:1]([O:7][CH2:8][C@@H:9]([C:17]([O:19]CC1C=CC=CC=1)=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]>[Pd].C(O)C>[C:1]([O:7][CH2:8][C@@H:9]([C:17]([OH:19])=[O:18])[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 1

HCID 53948101benzyl O-acetoacetyl-N-trifluoroacetyl-L-serinate

Product 1

HCID 18640001O-acetoacetyl-N-trifloroacetyl-L-serineYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl O-acetoacetyl-N-trifluoroacetyl-L-serinate (320 mg) and 10% palladium on activated carbon (40 mg) in ethanol (10 ml) was hydrogenated under hydrogen at one atom for 20 minutes. The mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals) and the filtrate was concentrated to give O-acetoacetyl-N-trifloroacetyl-L-serine (232 mg).

Workup

  1. filtrationThe mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals)
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4c02b58b79d64e88a2ff0a6eecbabd51
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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