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

HRID 1154195노트

반응식

HRID 1154195 반응식
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]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 136460587HCID 136460587, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-052f4ddd64d64f8083ad1c755085fd7d
출처 데이터셋
uspto-grants-1984_12
특허 번호
US04487927

반응 노트

불러오는 중…