反応 #56298

ord-5bcec5459bea4f9280758bd1ed364f42

反応方程式

O=P(O)(O)O
phosphoric acid
CCOC(=O)NS(=O)(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1
7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid
[N-]=[N+]=[N-].[Na+]
sodium azide
O=C([O-])O.[Na+]
sodium bicarbonate
→
[N-]=[N+]=NCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1
7β-(thienylacetamido)-3-azidomethyl-3-cephem-4-carboxylic acid

反応物

O=P(O)(O)O
phosphoric acid
CCOC(=O)NS(=O)(=O)c1ccccc1C(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)Cc3cccs3)[C@H]2SC1
7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid
[N-]=[N+]=[N-].[Na+]
sodium azide
O=C([O-])O.[Na+]
sodium bicarbonate

試薬

なし

溶媒

O=P([O-])([O-])[O-]
phosphate

反応条件

温度
60°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度After cooling
  2. 2
    抽出extracted with ethyl acetate
  3. 3
    乾燥The ethyl acetate layer is dried
  4. 4
    濃縮concentrated under reduced pressure
  5. 5
    その他The residue is triturated with ether

実験手順

7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid-etherate (619 mg), sodium azide (100 mg) and sodium bicarbonate (84 mg) are dissolved in phosphate buffer solution (pH 6.4) (10 ml) and the mixture is stirred at 60° C. for one hour. After cooling, the reaction mixture is acidified by phosphoric acid and extracted with ethyl acetate. The ethyl acetate layer is dried and concentrated under reduced pressure. The residue is triturated with ether. The procedure provides 7β-(thienylacetamido)-3-azidomethyl-3-cephem-4-carboxylic acid.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04224441uspto-grants-1980_09