Hydrochloric Acid → HCID 131717683, compound

HRID 2380295Notes

Reaction equation

HRID 2380295 reaction equation
FC(F)(F)C([O-])=O.FC(F)(F)C(O)=O.[NH2:15][C@@H:16]1[C:37](=[O:38])[N:18]2[C:19]([C:34]([OH:36])=[O:35])=[C:20]([CH2:23][N+:24]3[N:28]4[CH2:29][CH2:30][C:31](=[O:33])[NH:32][C:27]4=[CH:26][CH:25]=3)[CH2:21][S:22][C@H:17]12.CN(C)C=O.[NH2:44][C:45]1[S:46][CH:47]=[C:48]([C:50](=[N:63][O:64][CH3:65])[C:51](N2C3C=CC=CC=3[N+]([O-])=N2)=[O:52])[N:49]=1.Cl>O1CCCC1.O>[NH2:44][C:45]1[S:46][CH:47]=[C:48]([C:50](=[N:63][O:64][CH3:65])[C:51]([NH:15][C@@H:16]2[C:37](=[O:38])[N:18]3[C:19]([C:34]([O-:36])=[O:35])=[C:20]([CH2:23][N+:24]4[N:28]5[CH2:29][CH2:30][C:31](=[O:33])[NH:32][C:27]5=[CH:26][CH:25]=4)[CH2:21][S:22][C@H:17]23)=[O:52])[N:49]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 534275812-(2-Amino-1,3-thiazol-4-yl)-2-(methoxyimino)-1-(3-oxo-1H-1lambda~5~,2,3-benzotriazol-1-yl)ethan-1-oneHCID 131717685HCID 131717685, compound

Product 1

HCID 131717683HCID 131717683, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7β-amino-3-(5-oxo-4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate bis(trifluoroacetate) (1.5 g) in a mixture of tetrahydrofuran (40 ml) and water (20 ml) was added N,N-dimethylformamide solvate (1.02 g) of 1-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetyl]-1H-benzotriazol-3-oxide at ambient temperature. The mixture was stirred for 4 hours at pH 7. The solution was adjusted to pH 2 with 1N hydrochloric acid, washed with ethyl acetate five times and evaporated in vacuo to remove ethyl acetate. The solution was subjected to column chromatography on HP-20 and the elution was carried out with 5% aqueous isopropyl alcohol. The objective fraction was collected and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(5-oxo-4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate (syn isomer) (261 mg).

Workup

  1. washwashed with ethyl acetate five times
  2. customevaporated in vacuo
  3. customto remove ethyl acetate
  4. washthe elution
  5. customThe objective fraction was collected

Sources & evidence

ORD record
ord-2ccbc187bf044ed79df8c0924afaaf06
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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