Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate → Racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid

HRID 1376841Notes

Reaction equation

HRID 1376841 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:53][O:54][CH3:55])[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][CH2:51][CH3:52])=[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:53][O:54][CH3:55])[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][CH2:51][CH3:52])=[O:49])=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1

Participants

3

Reactant 1

HCID 53798384Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Product 1

HCID 54438830Racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acidYield 55.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 200 mg of the product of Step B dissolved in 4 ml of 66% formic acid was stirred at 50° C. for 2 hours, after which the solution was cooled and filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was re-dissolved in ethanol. The solvent was evaporated and 20 ml of ether were added with stirring for 30 minutes. Then, the crude products was separated and chromatographed on silica and eluted with a mixture of methylene chloride and methanol (8-2). After crystallization from ether, 70 mg of racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(ethoxycarbonylmethylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid melting at >210° C. (decomposes) were obtained.

Workup

  1. temperatureafter which the solution was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. dissolutionthe residue was re-dissolved in ethanol
  5. customThe solvent was evaporated
  6. addition20 ml of ether were added
  7. stirringwith stirring for 30 minutes
  8. customThen, the crude products was separated
  9. customchromatographed on silica
  10. washeluted with a mixture of methylene chloride and methanol (8-2)
  11. customAfter crystallization from ether

Sources & evidence

ORD record
ord-ae9747bf9d2f4c4c9a2c836262cf18d8
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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