Sodium Bicarbonate → HCID 131717282, compound

HRID 1030055Notes

Reaction equation

HRID 1030055 reaction equation
S(O)([O-])(=O)=O.[NH2:6][C:7]1[S:11][N:10]=[C:9]([C:12](=[N:40][O:41][CH3:42])[C:13]([NH:15][CH:16]2[C:38](=[O:39])[N:18]3[C:19]([C:35]([OH:37])=[O:36])=[C:20]([CH2:23][N+:24]45[CH2:31][CH2:30][C:27]([C:32](=[O:34])[NH2:33])([CH2:28][CH2:29]4)[CH2:26][CH2:25]5)[CH2:21][S:22][C@H:17]23)=[O:14])[N:8]=1.[C:43](=O)([O-:45])[OH:44].[Na+:47]>CC(C)=O>[C:43]([NH:6][C:7]1[S:11][N:10]=[C:9]([C:12](=[N:40][O:41][CH3:42])[C:13]([NH:15][CH:16]2[C:38](=[O:39])[N:18]3[C:19]([C:35]([O-:37])=[O:36])=[C:20]([CH2:23][N+:24]45[CH2:31][CH2:30][C:27]([C:32](=[O:34])[NH2:33])([CH2:26][CH2:25]4)[CH2:28][CH2:29]5)[CH2:21][S:22][C@H:17]23)=[O:14])[N:8]=1)([O-:45])=[O:44].[Na+:47]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 131717284HCID 131717284, compound

Product 1

HCID 131717282HCID 131717282, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of crystals of 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(4-carbamoyl-1-quinuclidinio)methyl-3-cephem-4-carboxylate sulfate (syn isomer) (500 mg) in 50% aqueous acetone (4 ml) was added sodium hydrogencarbonate (323 mg) at ambient temperature. Carbonic acid gas was bubbled into the mixture for four hours and diluted with water. The resulting mixture was chromatographed on non-ionic adsorption resin "Diaion HP-20" (50 ml) eluting with water. The desired fractions were collected and lyophilized to give sodium 7-[2-(5-carboxylatoamino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(4-carbamoyl-1-quinuclidinio)methyl-3-cephem-4-carboxylate (syn isomer) (239.6 mg).

Workup

  1. customCarbonic acid gas was bubbled into the mixture for four hours
  2. additiondiluted with water
  3. customThe resulting mixture was chromatographed on non-ionic adsorption resin "Diaion
  4. wash" (50 ml) eluting with water
  5. customThe desired fractions were collected

Sources & evidence

ORD record
ord-a84d700f7a6f4859a44e70106dcf301b
Source dataset
uspto-grants-1992_04
Patent number
US05104866

Reaction notes

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