Hydrochloric Acid → HCID 131718938, compound

HRID 1734257Notes

Reaction equation

HRID 1734257 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:38][O:39][CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:10]([NH:12][C@@H:13]2[C:36](=[O:37])[N:15]3[C:16]([C:33]([O-:35])=[O:34])=[C:17]([CH2:20][N+:21]([CH3:32])([CH3:31])[CH2:22][C:23]4[NH:24][CH:25]=[C:26]([OH:30])[C:27](=[O:29])[CH:28]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO.O>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:38][O:39][CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C:10]([NH:12][C@@H:13]2[C:36](=[O:37])[N:15]3[C:16]([C:33]([O-:35])=[O:34])=[C:17]([CH2:20][N+:21]([CH3:32])([CH3:31])[CH2:22][C:23]4[NH:24][CH:25]=[C:26]([OH:30])[C:27](=[O:29])[CH:28]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131718940HCID 131718940, compound

Product 1

HCID 131718938HCID 131718938, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of 7β-[2-(2-formamidothiazol-4-yl)- 2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl}ammonio]methyl-3-cephem-4-carboxylate (syn isomer) (0.70 g) in methanol (35 ml) was added conc. hydrochloric acid (0.53 ml). After being stirred at ambient temperature, the reaction mixture was diluted with water (50 ml) and methanol was evaporated under reduced pressure. The resulting aqueous solution was adjusted to pH 1.0 and subjected to column chromatography on Diaion HP-20 (50 ml). The column was washed with water and the elution was carried out with 40% aqueous isopropanol. The fractions containing the object compound was lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[N,N-dimethyl-N-{(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl} ammonio]methyl-3-cephem-4-carboxyl ate (syn isomer) (0.53 g).

Workup

  1. customwas evaporated under reduced pressure
  2. washThe column was washed with water
  3. washthe elution
  4. additionThe fractions containing the object compound

Sources & evidence

ORD record
ord-77240e1b5115438285c3580eb6018981
Source dataset
uspto-grants-1996_07
Patent number
US05532354

Reaction notes

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