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

HRID 1376836Notes

Reaction equation

HRID 1376836 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:56][O:57][CH3:58])[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][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([N+:53]([O-:55])=[O:54])[CH:48]=2)=[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:56][O:57][CH3:58])[C:27]([NH:29][C@H:30]2[C:37](=[O:38])[N:36]3[C@@H:31]2[CH2:32][S:33][C:34]([S:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([N+:53]([O-:55])=[O:54])[CH:48]=2)=[C:35]3[C:39]([OH:41])=[O:40])=[O:28])[N:25]=1

Participants

3

Reactant 1

HCID 53941303Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

Product 1

HCID 131720174Racemic cis 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acidYield 44.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

286 mg of the product of Step B dissolved in 3 ml of 66% formic acid were stirred for 4 hours and then filtered. The filtrate was concentrated to dryness and the residue was dissolve in an acetonitrile-ethanol mixture. The solvents were evaporated and the residue was crystallized from isopropanol to obtain 82 mg of racemic cis 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid. 65 mg of the same product were recovered from the mother liquors and melted at 180°-200° C. (with decomposition).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness
  3. dissolutionthe residue was dissolve in an acetonitrile-ethanol mixture
  4. customThe solvents were evaporated
  5. customthe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-7d1b36e902984455adfcd161efd33983
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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