Dimethylformamide → HCID 131715761, compound

HRID 1194603Notes

Reaction equation

HRID 1194603 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)C=O.[CH3:11][O:12][N:13]=[C:14]([C:18]1[N:19]=[C:20]([NH:23][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:21][CH:22]=1)[C:15](O)=[O:16].[NH2:43][CH:44]1[C:69](=[O:70])[N:46]2[C:47]([C:53]([O:55][CH:56]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[O:54])=[C:48]([CH2:51][Cl:52])[CH2:49][S:50][C@H:45]12>C(Cl)Cl.C(OCC)(=O)C>[Cl:52][CH2:51][C:48]1[CH2:49][S:50][C@@H:45]2[CH:44]([NH:43][C:15](=[O:16])[C:14](=[N:13][O:12][CH3:11])[C:18]3[N:19]=[C:20]([NH:23][C:24]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[S:21][CH:22]=3)[C:69](=[O:70])[N:46]2[C:47]=1[C:53]([O:55][CH:56]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:54]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 131715761HCID 131715761, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

6.35 ml (68 mmol) of phosphorus oxychloride was added to 20 ml of dry ethyl acetate. 5.28 ml (68 mmol) of N,N-dimethylformamide was dropwise added thereto at 0° C., and the mixture was stirred at the same temperature for 15 minutes. To this solution, 180 ml of dry methylene chloride was added. 25.2 g (57 mmol) of 2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (syn-isomer) was added thereto at 0° C., and the mixture was stirred for 30 minutes. Then, to this solution, 23.6 g (57 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate was added, and the mixture was stirred at 0° C. for 2 hours. The reaction solution was adjusted to pH 7.0, and insoluble substances were filtered off. The filtrate was washed sequentially with a 5% sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 44.5 g (yield: 99%) of benzhydryl 3-chloromethyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (syn-isomer).

Workup

  1. stirringat 0° C., and the mixture was stirred for 30 minutes
  2. stirringthe mixture was stirred at 0° C. for 2 hours
  3. filtrationwere filtered off
  4. washThe filtrate was washed sequentially with a 5% sodium hydrogen carbonate aqueous solution
  5. dry with materiala saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11d8fe824db5415abd3ef5c08524df16
Source dataset
uspto-grants-1989_03
Patent number
US04814328

Reaction notes

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