Triethyl phosphonoacetate → Ethenyl-3-cephem-4-carboxylic acid

HRID 341907

反応式

HRID 341907 の反応式
N[CH:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6](C=O)[CH2:7][S:8][C@H:3]12.[CH2:16](OP(CC(OCC)=O)(=O)OCC)[CH3:17]>C1COCC1>[CH:16]([CH:7]1[CH:6]=[C:5]([C:11]([OH:13])=[O:12])[N:4]2[C:14](=[O:15])[CH2:2][C@H:3]2[S:8]1)=[CH2:17]

参加物

4

反応物 2

HCID 13345Triethyl phosphonoacetateHCID 872037627-Amino-3-formyl-3-cephem-4-carboxylic acid

生成物 1

HCID 70435117Ethenyl-3-cephem-4-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of 200 mg of 7-amino-3-formyl-3-cephem-4-carboxylic acid in 2 ml of THF is treated at room temperature with 1.08 ml of BSA. The reaction mixture is stirred at room temperature for 10 minutes. A clear solution is obtained containing N,O-bistrimethylsilyl-7-amino-3-formyl-3-cephem-4-carboxylic acid. The solution is cooled to 0° and treated dropwise with a mixture of 197 mg of diethylethoxycarbonylmethyl-phosphonate and 98 mg of potassium tert.butylate in 2 ml of THF. After 18 hours stirring at 0° the reaction mixture is worked up as described in example 23). 39 mg (15.5%) of 7-amino-3[E)-2-ethoxycarbonyl]ethenyl-3-cephem-4-carboxylic acid as a brown coloured powder are thus obtained.

後処理

  1. additionis treated at room temperature with 1.08 ml of BSA
  2. customA clear solution is obtained
  3. temperatureThe solution is cooled to 0°
  4. stirringAfter 18 hours stirring at 0° the reaction mixture

出典と根拠

ORDレコード
ord-f3a5dfb836a2485c9dd33e0543d90d87
出典データセット
uspto-grants-1999_01
特許番号
US05856474

関連ノート

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