Diketene → benzyl O-acetoacetyl-N-trifluoroacetyl-L-serinate

HRID 2165228Notes

Reaction equation

HRID 2165228 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([NH:5][C@H:6]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH2:7][OH:8])=[O:4].[CH2:21]=[C:22]1[O:26][C:24](=[O:25])[CH2:23]1>O1CCCC1>[C:24]([O:8][CH2:7][C@@H:6]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[NH:5][C:3](=[O:4])[C:2]([F:19])([F:20])[F:1])(=[O:25])[CH2:23][C:22]([CH3:21])=[O:26]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 14357546benzyl trifluoroacetyl-L-serinate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzyl trifluoroacetyl-L-serinate (500 mg) and diketene (0.1 ml) in tetrahydrofuran (10 ml) was heated with reflux overnight. The solvent was distilled off and the residue was diluted with ethyl acetate and washed successively with water and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was chromatographed on silica gel eluting successively with methylene chloride and a 4:1 mixture of methylene chloride and acetone to give benzyl O-acetoacetyl-N-trifluoroacetyl-L-serinate (320 mg).

Workup

  1. temperaturewith reflux overnight
  2. distillationThe solvent was distilled off
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed successively with water and brine
  5. dry with materialAfter drying over sodium sulfate
  6. extractionthe ethyl acetate extract
  7. filtrationwas filtered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel eluting successively with methylene chloride
  10. additiona 4:1 mixture of methylene chloride and acetone

Sources & evidence

ORD record
ord-143a4dfafdef4e2486e92290b600bd1e
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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