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Methanol → HCID 178477374、化合物

HRID 1074248
ノート
印刷プレビュー

反応式

HRID 1074248 の反応式
P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.[CH:13]([O:26][C:27]([C:29]1[N:34]2[C:35](=[O:46])[C@@H:36]([NH:37]C(=O)CC3SC=CC=3)[C@H:33]2[S:32][CH2:31][C:30]=1[CH:47]([S:49][C:50]1[NH:54][N:53]=[N:52][N:51]=1)[CH3:48])=[O:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CO>C(Cl)Cl.O>[CH:13]([O:26][C:27]([C:29]1[N:34]2[C:35](=[O:46])[CH:36]([NH2:37])[C@H:33]2[S:32][CH2:31][C:30]=1[CH:47]([S:49][C:50]1[NH:54][N:53]=[N:52][N:51]=1)[CH3:48])=[O:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 178477370HCID 178477370、化合物

生成物 1

HCID 178477374HCID 178477374、化合物収率 64%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
3 回

反応条件

温度
-10 °C

実験手順

To a suspension of 6.25 g of phosphorus pentachloride in 45 ml of anhydrous methylene chloride cooled at -10° C., is added 20 ml of anhydrous methylene chloride solution containing 2.4 g of pyridine and the mixed solution is stirred for 30 minutes. To the solution is dropwise added a solution of 9.3 g of 7β-(2-thienylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester in 30 ml of anhydrous methylene chloride during 30 minutes under stirring and keeping at -20° C.--10° C. The mixture is further stirred for 2 hours at the same temperature and then cooled to -30° C.--20° C., followed by adding dropwise 56 ml of methanol. Thus obtained solution is stirred for 30 minutes, keeping the temperature of the solution between -5° C. and 5° C., and 60 ml of water is added dropwise thereto, followed by further stirring for 30 minutes. Methylene chloride layer is washed with saturated aq. NaCl solution and concentrated. To the concentrate is added a mixture of water and ethyl acetate under stirring to give 4.746 g of 7-amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid benzhydryl ester as a crystal. Yield 64.0%.

後処理

  1. stirringunder stirring
  2. customkeeping at -20° C.--10° C
  3. stirringThe mixture is further stirred for 2 hours at the same temperature
  4. temperaturecooled to -30° C.--20° C.
  5. stirringThus obtained solution is stirred for 30 minutes
  6. additionis added dropwise
  7. stirringby further stirring for 30 minutes
  8. washMethylene chloride layer is washed with saturated aq. NaCl solution
  9. concentrationconcentrated
  10. additionTo the concentrate is added
  11. additiona mixture of water and ethyl acetate
  12. stirringunder stirring

出典と根拠

ORDレコード
ord-2914dfac6fe64dc3b16c53b2ee175b21
出典データセット
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04973684

反応ノート

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