Trifluoroacetic acid → Trifluoroacetic acid

HRID 1088066노트

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HRID 1088066 반응식
P(Cl)(Cl)(Cl)=O.C[N+](C)=CCl.[Cl-].[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH:26]2[CH2:30][CH2:29][CH:28]=[CH:27]2)[C:21]([OH:23])=O)[N:19]=1)=[O:13].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[NH2:38][C@@H:39]1[C:56](=[O:57])[N:41]2[C:42]([C:53]([O-:55])=[O:54])=[C:43]([CH2:46][N+:47]3[N:48]([CH3:52])[CH:49]=[CH:50][CH:51]=3)[CH2:44][S:45][C@H:40]12.C(OC(C)C)(C)C>C(OCC)(=O)C>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:24][O:25][CH:26]2[CH2:30][CH2:29][CH:28]=[CH:27]2)[C:21]([NH:38][C@@H:39]2[C:56](=[O:57])[N:41]3[C:42]([C:53]([O-:55])=[O:54])=[C:43]([CH2:46][N+:47]4[N:48]([CH3:52])[CH:49]=[CH:50][CH:51]=4)[CH2:44][S:45][C@H:40]23)=[O:23])[N:19]=1)=[O:13]

참가 물질

9

반응물 6

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chloride2회HCID 538228722-(2-Cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetic acidHCID 178480378HCID 178480378, 화합물

생성물 2

HCID 6422Trifluoroacetic acidHCID 178480381HCID 178480381, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

N,N-Dimethylformamido (0.75 g) and phosphoryl chloride (1.57 ml) were mixed to prepare Vilsmeier reagent in a usual manner, and the resultant Vilsmeier reagent was suspended in dry ethyl acetate (22 ml). To the suspension was added 2-(2-formamidothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino) acetic acid (A isomer) (syn isomer) (2.3 g) under ice-cooling with stirring, and then the mixture was stirred for an hour to prepare an activated acid solution. To a solution of bis(trifluoroacetic acid )salts of 7β-amino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (4.7 g) and N-mono(trimethylsilyl)acetamido (11.8 g) in ethyl acetate (50 ml) was added the activated acid solution prepared above at 3° C. After stirring at the same temperature for an hour, the mixture was poured into diisopropyl ether (500 ml). The precipitates were collected by filtration and successively washed with diisopropyl ether to give trifluoroacetic acid salt of 7β-[2-(2-formamidothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl- 3-cephem-4-carboxylate (A isomer) (syn isomer) (6.02 g).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred for an hour
  3. customto prepare an activated acid solution
  4. customprepared above at 3° C
  5. stirringAfter stirring at the same temperature for an hour
  6. filtrationThe precipitates were collected by filtration
  7. washsuccessively washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-0361a0995f5e47e8a19a2cf90650f929
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04960766

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