Phosphorus oxychloride → Benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate

HRID 64751

반응식

HRID 64751 반응식
C[N+](C)=CCl.[Cl-].P(Cl)(Cl)(Cl)=O.[CH3:12][O:13][N:14]=[C:15]([C:19]1[N:20]=[C:21]([NH:24][CH:25]=[O:26])[S:22][CH:23]=1)[C:16]([OH:18])=O.Cl.[NH2:28][CH:29]1[C:56](=[O:57])[N:31]2[C:32]([C:40]([O:42][CH:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:33]([CH:36]=[C:37]([Cl:39])[Cl:38])[CH2:34][S:35][C@H:30]12>O1CCCC1.C(OCC)(=O)C.O.CN(C)C=O>[CH3:12][O:13][N:14]=[C:15]([C:19]1[N:20]=[C:21]([NH:24][CH:25]=[O:26])[S:22][CH:23]=1)[C:16]([NH:28][CH:29]1[C:56](=[O:57])[N:31]2[C:32]([C:40]([O:42][CH:43]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])=[C:33]([CH:36]=[C:37]([Cl:39])[Cl:38])[CH2:34][S:35][C@H:30]12)=[O:18]

참가 물질

9

반응물 4

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 27245112-(2-Formylamino-1,3-Thiazol-4-Yl)-2-(Methoxyimino)Acetic AcidHCID 88625735Benzhydryl 7-amino-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate hydrochloride

생성물 1

HCID 131714844Benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate수율 67.5%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a stirred suspension of Vilsmeier reagent prepared from N,N-dimethylformamide (0.56 ml) and phosphorus oxychloride (0.664 ml) in tetrahydrofuran (11 ml) in a usual manner was added 2-methoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (1.38 g) under ice-cooling and the mixture was stirred for 30 minutes at the same temperature. To a solution of benzhydryl 7-amino-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate hydrochloride (2.5 g) and monotrimethylsilylacetamide (3.95 g) in ethyl acetate (25 ml) was added the activated acid solution obtained above at -20° C. and mixture was stirred at -20° to -10° C. for 30 minutes. After water and ethyl acetate were added to the resultant mixture, the separated organic layer was washed in turn with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2,2-dichlorovinyl)-3-cephem-4-carboxylate (syn isomer) (2.28 g).

후처리

  1. temperaturecooling
  2. customobtained above at -20° C. and mixture
  3. stirringwas stirred at -20° to -10° C. for 30 minutes
  4. washthe separated organic layer was washed in turn with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solution was evaporated in vacuo

출처 및 근거

ORD 기록
ord-0cc3ce44be43458c812d219a359ea1f3
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609730

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