Trifluoroacetic acid → 7beta-amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid

HRID 28019Notes

Reaction equation

HRID 28019 reaction equation
C(OC([NH:8][C@@H:9]1[C:38](=[O:39])[N:11]2[C:12]([C:35]([OH:37])=[O:36])=[C:13]([CH2:16][O:17][C:18](=[O:34])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25](=[O:33])(=[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>CCOCC>[NH2:8][C@@H:9]1[C:38](=[O:39])[N:11]2[C:12]([C:35]([OH:37])=[O:36])=[C:13]([CH2:16][O:17][C:18](=[O:34])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[S:25](=[O:33])(=[O:32])[NH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][S:15][C@H:10]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70582695HCID 70582695, compound

Product 1

HCID 705835287beta-amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7β-(t-Butoxycarbonyl)amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (2.2 g) is dissolved in ice cooled solution of trifuoroacetic acid (20 ml) and the mixture is stirred for 20 minutes. Then trifluoroacetic acid is taken off under reduced pressure and viscous residue is obtained. The residue becomes solid upon addition of ether (50 ml). The solid is triturated, collected by filtration, washed with ether and dried over phosphorus pentoxide. The procedure provides 7β-amino-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (1.55 g).

Workup

  1. customviscous residue is obtained
  2. customThe solid is triturated
  3. filtrationcollected by filtration
  4. washwashed with ether
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-5a172908a35746a1ae556a5be665f22e
Source dataset
uspto-grants-1980_09
Patent number
US04224441

Reaction notes

Loading…