HCID 131717597, compound → HCID 131717596, compound

HRID 467256Notes

Reaction equation

HRID 467256 reaction equation
Cl.[CH3:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:13]([NH:14][C:15](=[O:26])[C:16]([C:20]3[N:21]=[C:22]([NH2:25])[S:23][CH:24]=3)=[N:17][O:18][CH3:19])[C:12](=[O:27])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10]>C(O)C>[CH3:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:13]([NH:14][C:15](=[O:26])[C:16]([C:20]3[N:21]=[C:22]([NH2:25])[S:23][CH:24]=3)=[N:17][O:18][CH3:19])[C:12](=[O:27])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 131717597HCID 131717597, compound

Product 1

HCID 131717596HCID 131717596, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The said hydrochloride was suspended at 20° C. in 820 ml of 90% ethanol and the suspension was refluxed while 1 ml of 22° Be was added thereto. The mixture was filtered hot and the filter was rinsed with 41 ml of 90% ethanol. 25 ml of triethylamine were added with stirring over 15 minutes to the filtrate at 45° to 50° C. and the mixture was then stirred at 18° to 20° C. for 2 hours and was vacuum filtered. The product was washed 3 times with 83 ml of ethanol and 3 times with 82 ml of demineralized water and dried at 40° C. under reduced pressure to obtain 66 g (64.6 g on dry basis) of the syn isomer of 3-methyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid. A second yield of 4.7 g of the product was obtained under the same conditions for a total yield of 69.3 g (75.1% yield).

Workup

  1. temperaturethe suspension was refluxed while 1 ml of 22° Be
  2. additionwas added
  3. filtrationThe mixture was filtered hot
  4. washthe filter was rinsed with 41 ml of 90% ethanol
  5. addition25 ml of triethylamine were added
  6. stirringthe mixture was then stirred at 18° to 20° C. for 2 hours
  7. filtrationfiltered
  8. washThe product was washed 3 times with 83 ml of ethanol and 3 times with 82 ml of demineralized water
  9. customdried at 40° C. under reduced pressure
  10. customto obtain
  11. dry with material66 g (64.6 g on dry basis) of the syn isomer of 3-methyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Sources & evidence

ORD record
ord-c66da3d21ad64b12ba07ef4311537034
Source dataset
uspto-grants-1992_10
Patent number
US05159070

Reaction notes

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