7beta-(t-Butoxycarbonyl)amino-3-[2-(N-tosylcarbamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid → HCID 70582400, compound

HRID 261717Notes

Reaction equation

HRID 261717 reaction equation
C(OC([NH:8][C@@H:9]1[C:42](=[O:43])[N:11]2[C:12]([C:39]([OH:41])=[O:40])=[C:13]([CH2:16][O:17][C:18](=[O:38])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:37])[NH:26][S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[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:42](=[O:43])[N:11]2[C:12]([C:39]([OH:41])=[O:40])=[C:13]([CH2:16][O:17][C:18](=[O:38])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:37])[NH:26][S:27]([C:30]3[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:14][S:15][C@H:10]12

Participants

3

Reactant 1

HCID 705836227beta-(t-Butoxycarbonyl)amino-3-[2-(N-tosylcarbamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid

Product 1

HCID 70582400HCID 70582400, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7β-(t-Butoxycarbonyl)amino-3-[2-(N-tosylcarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (631 mg) is dissolved in trifluoroacetic acid (2 ml) under ice-cooling. The solution is stirred for 20 minutes and concentrated under reduced pressure. To the residue, ether (20 ml) is added and the resultant solid is triturated. The powder thus obtained is collected by filtration, washed with ether and dried over phosphorus pentoxide. The procedure provides 7β-amino-3-[2-(N-tosylcarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (480 mg).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue, ether (20 ml) is added
  4. customthe resultant solid is triturated
  5. customThe powder thus obtained
  6. filtrationis collected by filtration
  7. washwashed with ether
  8. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-44d669d78396485f9e0c74dd0aea5711
Source dataset
uspto-grants-1979_08
Patent number
US04166178

Reaction notes

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