N,N-Dimethylaniline → HCID 131716196, compound

HRID 704951Notes

Reaction equation

HRID 704951 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:43]=[CH:44][C:45]=1[O:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH3:52])[CH2:11][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].[NH2:53][CH:54]1[C:79](=[O:80])[N:56]2[C:57]([C:63]([O:65][CH:66]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)=[O:64])=[C:58]([CH2:61][Cl:62])[CH2:59][S:60][C@H:55]12.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>>[Cl:62][CH2:61][C:58]1[CH2:59][S:60][C@@H:55]2[CH:54]([NH:53][C:15](=[O:16])[C:14](=[N:13][O:12][CH2:11][C:10]3[CH:43]=[CH:44][C:45]([O:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH3:52])=[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:9]=3)[C:18]3[N:19]=[C:20]([NH:23][C:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[S:21][CH:22]=3)[C:79](=[O:80])[N:56]2[C:57]=1[C:63]([O:65][CH:66]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:73]1[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=1)=[O:64]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylateHCID 53785634HCID 53785634, compound

Product 1

HCID 131716196HCID 131716196, compound

Procedure

1.0 g (1.4 mmol) of 2-[3,4-di(2-methoxyethoxymethoxy)benzyloxyimino]-2-(2-tritylaminothiazol-4-yl)acetic acid (syn-isomer) and 0.56 g (1.4 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate were dissolved in 0.77 ml (6.3 mmol) of N,N-dimethylaniline at 0° C., and 0.12 ml (1.7 mmol) of phosphorus oxychloride was dropwise added thereto. The mixture was stirred for 30 minutes and the reaction solution was washed with sequentially with 1 N hydrochloric acid, a 10% sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution. The water layer was further extracted with ethyl acetate, and the organic layer was added thereto. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain benzhydryl 3-chloromethyl-7-{2-[3,4-di(2-methoxyethoxymethoxy)benzyloxyimino]-2-(2-tritylaminothiazol-4-yl)acetamido}-3-cephem-4-carboxylate (syn-isomer), which was used for the next reaction without purification.

Workup

  1. washthe reaction solution was washed with sequentially with 1 N hydrochloric acid
  2. extractionThe water layer was further extracted with ethyl acetate
  3. additionthe organic layer was added
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-61ff8804d1504ba58510ca8a0da71a61
Source dataset
uspto-grants-1991_01
Patent number
US04988687

Reaction notes

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