Pyridine → HCID 86734230、化合物

HRID 1731221ノート

反応式

HRID 1731221 の反応式
[C:1]1([C:7]([NH:20][CH:21]2[C:37](=[O:38])[N:23]3[CH:24]([C:29](=O)[NH:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.[N-:51]=[N+:52]=[N-:53].CN(C)C(=[NH2+])N(C)C>O.C(Cl)(Cl)Cl.C(Cl)Cl>[C:1]1([C:7]([NH:20][CH:21]2[C:37](=[O:38])[N:23]3[CH:24]([C:29]4[N:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[N:53]=[N:52][N:51]=4)[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]23)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 706052636-(triphenylmethylamino)-2,2-dimethyl-3-(N-[ethoxycarbonyl]carbamoyl)penamHCID 178484365HCID 178484365、化合物

生成物 1

HCID 86734230HCID 86734230、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 529 mg. (1 mmole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[ethoxycarbonyl]carbamoyl)penam and 240 mg. (3 mmole) of pyridine, in 25 ml. of methylene chloride, is added 208 mg. (1 mmole) of phosphorus pentachloride, at 0° C. The reaction mixture is stirred at 0° C. for 0.5 hour and then at ca. 25° C. for 2 hours. The solvents and the excess pyridine are then removed by evaporation in vacuo, and the residue is re-dissolved in 15 ml. of chloroform. The latter chloroform solution is cooled to 0° C., and 0.47 g. (3 mmole) of tetramethylguanidinium azide is added in several small portions with stirring. Stirring is continued for 2 hours at ambient temperature, and then to the reaction mixture is added a further 15 ml. of chloroform followed by 30 ml. of water. The pH is adjusted to 6.5, and then the chloroform layer is removed. The chloroform solution is washed with water followed by brine, and then it is dried using anhydrous sodium sulfate. Removal of the solvent by evaporation in vacuo affords crude 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[ethoxycarbonyl]tetrazol-5-yl)penam. The crude product is purified further by chromatography using silica gel.

後処理

  1. customat 0° C
  2. waitat ca. 25° C. for 2 hours
  3. customThe solvents and the excess pyridine are then removed by evaporation in vacuo
  4. dissolutionthe residue is re-dissolved in 15 ml
  5. temperatureThe latter chloroform solution is cooled to 0° C.
  6. stirringwith stirring
  7. stirringStirring
  8. waitis continued for 2 hours at ambient temperature
  9. additionto the reaction mixture is added a further 15 ml
  10. customthe chloroform layer is removed
  11. washThe chloroform solution is washed with water
  12. customit is dried
  13. customRemoval of the solvent
  14. customby evaporation in vacuo

出典と根拠

ORDレコード
ord-9e8d4f9a9fe14ec08c5b86e2b7cc6126
出典データセット
uspto-grants-1976_11
特許番号
US03994939

反応ノート

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