HCID 70563378, compound → HCID 70566100, compound

HRID 127654Notes

Reaction equation

HRID 127654 reaction equation
[N+](C1C=CC(C[O:9][C:10]([C:12]2[N:17]3[C:18](=[O:31])[C@@H:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]3[S:15][CH2:14][C:13]=2[S:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:11])=CC=1)([O-])=O>C(O)(=O)C.[Zn]>[CH2:33]([S:32][C:13]1[CH2:14][S:15][C@@H:16]2[C@H:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:31])[N:17]2[C:12]=1[C:10]([OH:11])=[O:9])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 1

HCID 70563378HCID 70563378, compound

Product 1

HCID 70566100HCID 70566100, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

425 mg of activated zinc powder are added to a solution of 425 mg (0.72 mmol) of 3-benzylthio-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid p-nitrobenzyl ester in 40 ml of glacial acetic acid and the mixture is stirred vigorously for 2 hours at room temperature and under nitrogen. The solvent is removed in vacuo and the residue is stirred with ethyl acetate and filtered. The solution is extracted with aqueous sodium bicarbonate solution and water. The combined aqueous phases are washed with ethyl acetate, acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered and evaporated in vacuo. The residue is chromatographed on silica gel with toluene containing 10% of acetone and gives 3-benzylthio-7β-phenoxyacetylamino-3-cephem-4-carboxylic acid; [α]D20° =+19±1° (c=0.8; chloroform); IR spectrum (methylene chloride): characteristic bands at 5.61 and 5.90μ.

Workup

  1. customThe solvent is removed in vacuo
  2. stirringthe residue is stirred with ethyl acetate
  3. filtrationfiltered
  4. extractionThe solution is extracted with aqueous sodium bicarbonate solution and water
  5. washThe combined aqueous phases are washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic phase is dried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue is chromatographed on silica gel with toluene containing 10% of acetone

Sources & evidence

ORD record
ord-1dbea0985f99406fa215d04cf36ed475
Source dataset
uspto-grants-1981_03
Patent number
US04256739

Reaction notes

Loading…