N,N-Dimethylaniline → HCID 131715766, compound

HRID 1194606Notes

Reaction equation

[CH:1]([O:14][C:15]([C:17]([CH3:50])([O:19][N:20]=[C:21]([C:25]1[N:26]=[C:27]([NH:30][C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[S:28][CH:29]=1)[C:22](O)=[O:23])[CH3:18])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:51][CH:52]1[C:77](=[O:78])[N:54]2[C:55]([C:61]([O:63][CH:64]([C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[O:62])=[C:56]([CH2:59][Cl:60])[CH2:57][S:58][C@H:53]12.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(Cl)Cl>[Cl:60][CH2:59][C:56]1[CH2:57][S:58][C@@H:53]2[CH:52]([NH:51][C:22](=[O:23])[C:21](=[N:20][O:19][C:17]([C:15]([O:14][CH:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:16])([CH3:50])[CH3:18])[C:25]3[N:26]=[C:27]([NH:30][C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[S:28][CH:29]=3)[C:77](=[O:78])[N:54]2[C:55]=1[C:61]([O:63][CH:64]([C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)[C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:62]

Participants

Conditions

Temperature: -10 °C

Procedure

28 g (41 mmol) of 2-(1-benzhydryloxycarbonyl-1-methylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (syn-isomer) and 17 g (41 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate, were dissolved in 300 ml of dry methylene chloride, and 15.6 ml (123 mmol) of N,N-dimethylaniline was added thereto. The mixture was cooled to -10° C., and 4 ml (43 mmol) of phosphorus oxychloride was dropwise added thereto. The reaction solution was stirred at room temperature for 2.5 hours, and then concentrated under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed sequentially with 1N hydrochloric acid, 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 36 g (yield: 81%) of benzhydryl 3-chloromethyl-7-[2-(1-benzhydryloxycarbonyl-1-methylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (syn-isomer).

Workup

concentrationconcentrated under reduced pressure
extractionThe residue was extracted with ethyl acetate
washThe organic layer was washed sequentially with 1N hydrochloric acid
dry with materiala 5% sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9af6250835c24012b863c961f4373ac8
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04814328

Reaction notes

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