HCID 54354677, compound → HCID 88374011, compound

HRID 1376837Notes

Reaction equation

HRID 1376837 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][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)=[C:35]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[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][C:47]2[CH:48]=[CH:49][C:50]([O:53][CH3:54])=[CH:51][CH:52]=2)=[C:35]3[C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])=[O:28])[N:25]=1

Participants

3

Reactant 1

HCID 54354677HCID 54354677, compound

Product 1

HCID 88374011HCID 88374011, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

810 mg of the product of Step B dissolved in 10 ml of 66% formic acid were stirred for one hour at ambient temperature and filtered. The filtrate was concentrated to dryness under reduced pressure at less than 30° C. and the residue was dissolved in a mixture of acetonitrile and methanol. The solvents were evaporated and the residue was crystallized from ether to obtain 516 mg of racemic 1,1-dimethylethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(4-methoxyphenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness under reduced pressure at less than 30° C.
  3. dissolutionthe residue was dissolved in a mixture of acetonitrile and methanol
  4. customThe solvents were evaporated
  5. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-81afe8f094d24b24835388ae77a5c24e
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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