p-Toluenesulfonic acid monohydrate → HCID 178477368、化合物

HRID 224906

反応式

HRID 224906 の反応式
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[NH2:13][C@@H:14]1[C:32](=[O:33])[N:16]2[C:17]([C:29]([OH:31])=[O:30])=[C:18]([CH:21]([S:23][C:24]3[NH:28][N:27]=[N:26][N:25]=3)[CH3:22])[CH2:19][S:20][C@H:15]12>CO>[C:2]1([CH:12]([O:30][C:29]([C:17]2[N:16]3[C:32](=[O:33])[C@@H:14]([NH2:13])[C@H:15]3[S:20][CH2:19][C:18]=2[CH:21]([S:23][C:24]2[NH:25][N:26]=[N:27][N:28]=2)[CH3:22])=[O:31])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178477379HCID 178477379、化合物

生成物 1

HCID 178477368HCID 178477368、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2.09 g of p-toluenesulphonic acid monohydrate are added to a suspension of 5.0 g of 7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid (U.S. Pat. No. 3,516,997) in 200 ml of methanol, whilst stirring; this slowly produces a clear solution, which is concentrated under reduced pressure. Diethyl ether is added and the p-toluenesulphonic acid salt of 7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4carboxylic acid is filtered off. The salt is dissolved in 100 ml of dioxane and 2.5 g of diphenyldiazomethane are added in portions to the solution. The mixture is stirred for 18 hours at room temperature and concentrated under reduced pressure; 100 ml of an 0.1 N aqueous sodium bicarbonate solution are added to the residue and the mixture is extracted with twice 100 ml of ethyl acetate. The organic extracts are washed successively with water and with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. The crystallisation from diethyl ether gives 7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4-carboxylic acid diphenylmethyl ester, thin layer chromatogram (silica gel): Rf=0.21 (system: chloroform/ethyl acetate/acetic acid, 80:19:1); ultraviolet absorption spectrum (ethanol): λmax =269 mμ (ε=6,400); infrared absorption spectrum (in methylene chloride); characteristic bands at 2.93μ, 5.60μ and 6.15μ.

後処理

  1. customthis slowly produces a clear solution, which
  2. concentrationis concentrated under reduced pressure
  3. additionDiethyl ether is added
  4. filtrationthe p-toluenesulphonic acid salt of 7β-amino-3-(1-methyl-5-tetrazolylthiomethyl)-3-cephem-4carboxylic acid is filtered off
  5. dissolutionThe salt is dissolved in 100 ml of dioxane
  6. addition2.5 g of diphenyldiazomethane are added in portions to the solution
  7. concentrationconcentrated under reduced pressure
  8. addition100 ml of an 0.1 N aqueous sodium bicarbonate solution are added to the residue
  9. extractionthe mixture is extracted with twice 100 ml of ethyl acetate
  10. washThe organic extracts are washed successively with water and with a saturated aqueous sodium chloride solution
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated
  13. customThe crystallisation from diethyl ether

出典と根拠

ORDレコード
ord-f57a4d7b6d934ddaabea7dc286824f49
出典データセット
uspto-grants-1980_11
特許番号
US04234578

関連ノート

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