HCID 70583681, compound → 7beta-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid

HRID 261715Notes

Reaction equation

HRID 261715 reaction equation
C(OC([NH:8][C@@H:9]1[C:37](=[O:38])[N:11]2[C:12]([C:34]([OH:36])=[O:35])=[C:13]([CH2:16][O:17][C:18](=[O:33])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:32])[NH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][S:15][C@H:10]12)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C@@H:9]1[C:37](=[O:38])[N:11]2[C:12]([C:34]([OH:36])=[O:35])=[C:13]([CH2:16][O:17][C:18](=[O:33])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:32])[NH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][S:15][C@H:10]12

Participants

3

Reactant 1

HCID 70583681HCID 70583681, compound

Product 1

HCID 705826067beta-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acidYield 86.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7β-(t-Butoxycarbonyl)amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (275 mg) is dissolved in trifluoroacetic acid (2 ml) under ice-cooling and the mixture is stirred for 20 minutes. The solution is concentrated and to the residue, ether (20 ml) is added. The resultant precipitate is triturated, collected by filtration, washed with ether and dried over phosphorus pentoxide. The procedure provides 7β-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (195 mg). In NMR spectrum, this product is good agreement with the product obtained in Example 20.

Workup

  1. temperaturecooling
  2. concentrationThe solution is concentrated and to the residue, ether (20 ml)
  3. additionis added
  4. customThe resultant precipitate is triturated
  5. filtrationcollected by filtration
  6. washwashed with ether
  7. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-8ba35851554b4fe8831ca30b131ec700
Source dataset
uspto-grants-1979_08
Patent number
US04166178

Reaction notes

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