Hydrochloric Acid → 7beta-amino-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4carboxylate dihydrochloride

HRID 1609659Notes

Reaction equation

HRID 1609659 reaction equation
C([NH:3][C@@H:4]1[C:27](=[O:28])[N:6]2[C:7]([C:24]([O-:26])=[O:25])=[C:8]([CH2:11][N+:12]([CH3:23])([CH3:22])[CH2:13][C:14]3[NH:15][CH:16]=[C:17]([OH:21])[C:18](=[O:20])[CH:19]=3)[CH2:9][S:10][C@H:5]12)=O.[ClH:29].C(OCC)(=O)C>CO>[ClH:29].[ClH:29].[NH2:3][C@@H:4]1[C:27](=[O:28])[N:6]2[C:7]([C:24]([O-:26])=[O:25])=[C:8]([CH2:11][N+:12]([CH3:23])([CH3:22])[CH2:13][C:14]3[NH:15][CH:16]=[C:17]([OH:21])[C:18](=[O:20])[CH:19]=3)[CH2:9][S:10][C@H:5]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 883998567beta-formamido-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl) methyl}ammonio]methyl-3-cephem-4-carboxylate

Product 1

HCID 677480537beta-amino-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4carboxylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled suspension of 7β-formamido-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (1.225 g) in methanol (12 ml) was added dropwise conc. hydrochloric acid (0.83 ml) at 10° C. The mixture was warmed to room temperature and stirred for 2.5 hours. The mixture was poured into ethyl acetate (300 ml) and the precipitates were collected by filtration, washed with ethyl acetate and diisopropyl ether and dried in vacuo. The powder was dissolved in cold water (10 ml) and the resulting solution was chromatographed on Diaion HP-20 (10 ml) at 5° C. and the elution was carried out with cold water. To the eluate (24 ml) was added dropwise isopropyl alcohol (12 ml) under cooling and the mixture was allowed to stand overnight in a refrigerator. The resultant crystal was collected by filtration, washed with a cold mixture of isopropyl alcohol and water (10:1) and cold isopropyl alcohol, and dried in vacuo to give 7β -amino-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4carboxylate dihydrochloride (440 mg).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with ethyl acetate and diisopropyl ether
  3. customdried in vacuo
  4. dissolutionThe powder was dissolved in cold water (10 ml)
  5. customthe resulting solution was chromatographed on Diaion HP-20 (10 ml) at 5° C.
  6. washthe elution
  7. additionTo the eluate (24 ml) was added dropwise isopropyl alcohol (12 ml)
  8. temperatureunder cooling
  9. waitto stand overnight in a refrigerator
  10. filtrationThe resultant crystal was collected by filtration
  11. washwashed with a cold mixture of isopropyl alcohol and water (10:1) and cold isopropyl alcohol
  12. customdried in vacuo

Sources & evidence

ORD record
ord-be994a38ab634c67bea9eca69447c565
Source dataset
uspto-grants-1995_03
Patent number
US05401734

Reaction notes

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