Pyridine → Benzhydryl 7-amino-3-cephem-4-carboxylate

HRID 1604970ノート

反応式

HRID 1604970 の反応式
S1C=CC=C1CC([NH:9][CH:10]1[C:33](=[O:34])[N:12]2[C:13]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12)=O.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>[H-].[Ca+2].[H-]>[NH2:9][CH:10]1[C:33](=[O:34])[N:12]2[C:13]([C:17]([O:19][CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:18])=[CH:14][CH2:15][S:16][C@H:11]12

参加物

5

反応物 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 70617022HCID 70617022、化合物

生成物 1

HCID 12098365Benzhydryl 7-amino-3-cephem-4-carboxylate

試薬・触媒・溶媒 1

HCID 3033859Calcium hydride溶媒

実験手順

Benzhydryl 7-(2-thienylacetamido)-3-cephem-4-carboxylate (2.45 g. 5 mmol) was dissolved in calcium hydride dried benzene (130 ml) containing dry pyridine (0.59 g, 7.4 mmol). The solution was maintained at 0° and PCl5 (1.54 g, 7.4 mmol.) was added with stirring. The reaction mixture was stirred under nitrogen at 0° for three hours and then the solvent was removed in vacuo. Anhydrous methanol (260 ml) was added to the residue and the resultant mixture was allowed to stand two hours. The methanol was removed in vacuo and the residue was treated with 20% aqueous tetrahydrofuran. After 15 minuted the tetrahydrofuran was removed in vacuo and the aqueous residue was adjusted to pH 7.5 and extracted with ethyl acetate. The extracts were washed with water, dried over MgSO4 and evaporated to give the solid product which was triturated with chloroform-petroleum ether and dried under high vacuum.

後処理

  1. temperatureThe solution was maintained at 0°
  2. stirringThe reaction mixture was stirred under nitrogen at 0° for three hours
  3. customthe solvent was removed in vacuo
  4. additionAnhydrous methanol (260 ml) was added to the residue
  5. customThe methanol was removed in vacuo
  6. additionthe residue was treated with 20% aqueous tetrahydrofuran
  7. customwas removed in vacuo
  8. extractionextracted with ethyl acetate
  9. washThe extracts were washed with water
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customto give the solid product which
  13. customwas triturated with chloroform-petroleum ether
  14. customdried under high vacuum

出典と根拠

ORDレコード
ord-26af60a35dd04b59b505e500fd78bb0e
出典データセット
uspto-grants-1976_04
特許番号
US03948905

反応ノート

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