p-Toluenesulfonic acid → Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate

HRID 1154195ノート

反応式

HRID 1154195 の反応式
C1(N[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)CCCCC1.[CH:14](=[N:22][CH:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([OH:34])=[O:33])=[C:27]([CH2:30][OH:31])[CH2:28][S:29][C@H:24]12)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40](S(O)(=O)=O)=[CH:39][CH:38]=1>C(OCC)(=O)C>[CH:14](=[N:22][CH:23]1[C:35](=[O:36])[N:25]2[C:26]([C:32]([O:34][CH:47]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:33])=[C:27]([CH2:30][OH:31])[CH2:28][S:29][C@H:24]12)[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[OH:17]

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 136460587HCID 136460587、化合物

生成物 1

HCID 136460596Benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate収率 91.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a suspension of 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylic acid dicyclohexylamine salt (3 g) in ethyl acetate (60 ml) was added dropwise an ethyl acetate solution of p-toluenesulfonic acid (1.1 g) with stirring, and the reaction mixture was stirred for an hour at ambient temperature. After the precipitate was filtered off, the filtrate was treated with a solution of excess diphenyldiazomethane in ethyl acetate for an hour. The solvent was distilled off, and the residue was pulverized with diisopropyl ether, collected by filtration and dried to give benzhydryl 7-salicylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate (2.66 g).

後処理

  1. stirringthe reaction mixture was stirred for an hour at ambient temperature
  2. filtrationAfter the precipitate was filtered off
  3. additionthe filtrate was treated with a solution of excess diphenyldiazomethane in ethyl acetate for an hour
  4. distillationThe solvent was distilled off
  5. filtrationcollected by filtration
  6. customdried

出典と根拠

ORDレコード
ord-052f4ddd64d64f8083ad1c755085fd7d
出典データセット
uspto-grants-1984_12
特許番号
US04487927

反応ノート

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