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

HRID 28021Notes

Reaction equation

HRID 28021 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-6c56c5d8d468489080a200f90013b0c4
Source dataset
uspto-grants-1980_09
Patent number
US04224441

Reaction notes

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