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

HRID 2165228ノート

反応式

HRID 2165228 の反応式
[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]

参加物

4

反応物 2

HCID 12661DiketeneHCID 14357546benzyl trifluoroacetyl-L-serinate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-143a4dfafdef4e2486e92290b600bd1e
出典データセット
uspto-grants-1990_07
特許番号
US04939241

反応ノート

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