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

HRID 261712Notes

Reaction equation

HRID 261712 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.CCOCC>FC(F)(F)C(O)=O>[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 3283Diethyl EtherHCID 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 6422Trifluoroacetic acidSolvent2×

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 trifluoroacetic 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-ec01b87a0cb342f7831ef637908f643d
Source dataset
uspto-grants-1979_08
Patent number
US04166178

Reaction notes

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