N,N-Dimethylaniline → HCID 178525023, compound

HRID 1252313Notes

Reaction equation

HRID 1252313 reaction equation
[CH:1]([O:14][C:15]([C:17]1([O:22]/[N:23]=[C:24](/[C:28]2[N:29]=[C:30]([NH:33][C:34]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[S:31][CH:32]=2)\[C:25](O)=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[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.[NH2:53][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>C(Cl)Cl.O.C(Cl)(Cl)Cl>[CH:1]([O:14][C:15]([C:17]1([O:22]/[N:23]=[C:24](/[C:28]2[N:29]=[C:30]([NH:33][C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[S:31][CH:32]=2)\[C:25]([NH:53][CH:54]2[C:79](=[O:80])[N:56]3[C:57]([C:63]([O:65][CH:66]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)[C:73]4[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=4)=[O:64])=[C:58]([CH2:61][Cl:62])[CH2:59][S:60][C@H:55]23)=[O:26])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13239626Benzhydryl 7-Amino-3-chloromethyl-3-cephem-4-carboxylateHCID 21269519HCID 21269519, compound

Product 1

HCID 178525023HCID 178525023, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2.12 g (3 mmol) of (Z)-2-(1-benzhydryloxycarbonyl-1-cyclopentyloxyimino)-2-(2-tritylaminothiazol-4-yl) acetic acid and 1.24 g (3 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate were dissolved in 50 ml of methylene chloride, and 1.2 ml (9.6 mmol) of N,N-dimethylaniline was added under cooling with ice. Then, 0.29 ml (3.15 mmol) of phosphorus oxychloride was dropwise added thereto, and the mixture was stirred at the same temperature for 4 hours. 30 ml of chloroform and 30 ml of water was added to the reaction solution. The organic layer was washed with water and with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated to obtain the residue of the above identified compound, which was used for the subsequent reaction without purification.

Workup

  1. temperatureunder cooling with ice
  2. washThe organic layer was washed with water and with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto obtain the residue of the
  6. customwas used for the subsequent reaction without purification

Sources & evidence

ORD record
ord-4af7dd36e5344caa952f181e0911c29e
Source dataset
uspto-grants-1988_05
Patent number
US04742053

Reaction notes

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