HCID 88374011, compound → HCID 54059594, compound

HRID 1376838Notes

Reaction equation

HRID 1376838 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:36][O:37][CH3:38])[C:8]([NH:10][CH:11]2[C:18](=[O:19])[N:17]3[CH:12]2[CH2:13][S:14][C:15]([S:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[C:16]3[C:20]([O:22]C(C)(C)C)=[O:21])=[O:9])[N:6]=1>C(O)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:36][O:37][CH3:38])[C:8]([NH:10][CH:11]2[C:18](=[O:19])[N:17]3[CH:12]2[CH2:13][S:14][C:15]([S:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

3

Reactant 1

HCID 88374011HCID 88374011, compound

Product 1

HCID 54059594HCID 54059594, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

100 mg of the product of Step C dissolved in 2 ml of 66% formic acid were heated to 50° C. for 3 hours with stirring and was concentrated to dryness under reduced pressure. The residue was taken up in acetonitrile and the solvent was evaporated. The crude product was crystallized from ether and was then dissolved in methylene chloride with 10% of methanol. The solution was treated with active charcoal, then filtered and the filtrate was concentrated to dryness. The residue obtained was crystallized from ether to obtain 80 mg of syn isomer of racemic 7-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-8-oxo-3-(4-methoxyphenylthio)-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid melting at 185°-190° C. (with decomposition).

Workup

  1. concentrationwas concentrated to dryness under reduced pressure
  2. customthe solvent was evaporated
  3. customThe crude product was crystallized from ether
  4. dissolutionwas then dissolved in methylene chloride with 10% of methanol
  5. additionThe solution was treated with active charcoal
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to dryness
  8. customThe residue obtained
  9. customwas crystallized from ether

Sources & evidence

ORD record
ord-aae88ad89a124262a46809db44e49d59
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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