N,N-Dimethylaniline → HCID 141560563, compound

HRID 653563Notes

Reaction equation

HRID 653563 reaction equation
[CH:1]([O:14][C:15]([C:17]1([O:21]/[N:22]=[C:23](/[C:27]2[N:28]=[C:29]([NH:32][C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[S:30][CH:31]=2)\[C:24](O)=[O:25])[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.[NH2:52][CH:53]1[C:78](=[O:79])[N:55]2[C:56]([C:62]([O:64][CH:65]([C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)[C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)=[O:63])=[C:57]([CH2:60][Cl:61])[CH2:58][S:59][C@H:54]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:21]/[N:22]=[C:23](/[C:27]2[N:28]=[C:29]([NH:32][C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[S:30][CH:31]=2)\[C:24]([NH:52][CH:53]2[C:78](=[O:79])[N:55]3[C:56]([C:62]([O:64][CH:65]([C:66]4[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=4)[C:72]4[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=4)=[O:63])=[C:57]([CH2:60][Cl:61])[CH2:58][S:59][C@H:54]23)=[O:25])[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 20194650HCID 20194650, compound

Product 1

HCID 141560563HCID 141560563, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1.82 g (2.62 mmol) of [(Z)-2-(1-benzhydryloxycarbonyl-1-cyclobutoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid and 1.09 g (2.62 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate were dissolved in 40 ml of methylene chloride, and then 1.06 ml (8.39 mmol) of N,N-dimethylaniline and 0.26 ml (2.75 mmol) of phosphorus oxychloride were dropwise added thereto under cooling with ice. The mixture was stirred at the same temperature for 4 hours. To the reaction solution, 30 ml of chloroform and 30 ml of water were added. 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 a residue of the above-identified compound. The residue of the compound thus obtained was employed for the next 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 a residue of the above-identified compound
  6. customThe residue of the compound thus obtained
  7. customwas employed for the next reaction without purification

Sources & evidence

ORD record
ord-d03d25a2fd50458cbfcbd50ae242347e
Source dataset
uspto-grants-1987_06
Patent number
US04677100

Reaction notes

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