Ammonia → 7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

HRID 543542

反応式

HRID 543542 の反応式
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[SH:19][C:20]1[N:24]([CH3:25])[N:23]=[N:22][N:21]=1.P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.N>C(#N)C.O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:19][C:20]3[N:24]([CH3:25])[N:23]=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

参加物

7

反応物 4

HCID 222AmmoniaHCID 4413287-Aminocephalosporanic acidHCID 4432411Diphosphoryl tetrachlorideHCID 178482017HCID 178482017、化合物

生成物 1

HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid収率 87.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
-40 °C

実験手順

In 5.4 ml of acetonitrile were suspended 0.909 g of 7-ACA and 0.504 g of 5-mercapto-1-methyl-1H-tetrazole, and 0.256 g of water was added. The suspension was cooled at -40° C. under stirring, and 3.58 g of diphosphoryl tetrachloride was added dropwise to it at -50° to -35° C. The reaction mixture was stirred at -35° to 0° C. for 5 minutes after the dropwise addition and placed in a warm water bath at 40° C. to warm, followed by stirring at the same temperature for 20 minutes. The reaction solution was cooled over an ice water bath and, after the addition of 11 ml of cold water, it was adjusted to pH 4.0 with aqueous concentrated ammonia. The separated-out precipitate was recovered by filtration, washed with water and dried, thereby affording 0.956 g of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4 -carboxylic acid. The yield was 87.2%.

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred at -35° to 0° C. for 5 minutes
  3. additionafter the dropwise addition
  4. customplaced in a warm water bath at 40° C.
  5. temperatureto warm
  6. stirringby stirring at the same temperature for 20 minutes
  7. temperatureThe reaction solution was cooled over an ice water bath
  8. filtrationThe separated-out precipitate was recovered by filtration
  9. washwashed with water
  10. customdried

出典と根拠

ORDレコード
ord-0c37b6a37da346a8af4bc11f1565cc12
出典データセット
uspto-grants-1984_05
特許番号
US04446318

関連ノート

読み込み中…