HCID 54276616, compound → HCID 54248125, compound

HRID 1376842Notes

Reaction equation

HRID 1376842 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:55][O:56][CH3:57])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([S:46][CH2:47][C:48]([O:50]C(C)(C)C)=[O:49])=[C:35]3[C:39]([O:41]C(C)(C)C)=[O:40])=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:55][O:56][CH3:57])[C:27]([NH:29][CH:30]2[C:37](=[O:38])[N:36]3[CH:31]2[CH2:32][S:33][C:34]([S:46][CH2:47][C:48]([OH:50])=[O:49])=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1

Participants

3

Reactant 1

HCID 54276616HCID 54276616, compound

Product 1

HCID 54248125HCID 54248125, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 200 mg of the product of Step B in 4 ml of 66% aqueous formic acid was stirred for two hours and a half at 50° C. The cooled solution was filtered and evaporated. The residue was re-dissolved in a mixture of methanol and acetonitrile which was evaporated and the treatment was repeated. The residue was again dissolved in 5 ml of methanol and after carbon black was added, the mixture was stirred for a further 2 hours, then filtered. 30 ml of ether were added dropwise with stirring for hour and the white precipitate was separated and dried at 50° C. to obtain 53 mg of racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(carboxymethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid melting at 190° to 200° C. (with decomposition)

Workup

  1. customat 50° C
  2. filtrationThe cooled solution was filtered
  3. customevaporated
  4. dissolutionThe residue was re-dissolved in a mixture of methanol and acetonitrile which
  5. customwas evaporated
  6. dissolutionThe residue was again dissolved in 5 ml of methanol
  7. additionafter carbon black was added
  8. filtrationfiltered
  9. addition30 ml of ether were added dropwise
  10. stirringwith stirring for hour
  11. customthe white precipitate was separated
  12. customdried at 50° C.

Sources & evidence

ORD record
ord-ff58bf79304043dcbc7b2a93d61a29e5
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

Loading…