Carbon Dioxide → HCID 131717276, compound

HRID 1030053Notes

Reaction equation

HRID 1030053 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH2:34])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3].[C:35](=O)([O-:37])[OH:36].[Na+:39].C(=O)=O>CC(C)=O>[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:33]=[C:32]([NH:34][C:35]([O-:37])=[O:36])[S:31][N:30]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3].[Na+:39]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 516892Sodium BicarbonateHCID 131717273HCID 131717273, compound

Product 1

HCID 131717276HCID 131717276, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridinio)methyl-3-cephem-4-carboxylate (syn isomer) (1.15 g) in 50% aqueous acetone (9.2 ml) was added sodium hydrogencarbonate (193 mg) and dry ice (4.4 g) at room temperature. The mixture was stirred in a sealed tube for 5 hours. Acetone was removed under reduced pressure. The residual solution was chromatographed on non-ionic adsorption resin "Diaion HP-20" (Trademark, maker: Mitsubishi Chemical Industries) eluting with water. The desired fractions were collected and lyophilized to give sodium 7-[2-allyloxyimino-2-(5-carboxylatoamino-1,2,4-thiadiazol-3-yl)acetamido]-3-(1-pyridinio)methyl-3-cephem-4-carboxylate (syn isomer) (500 mg).

Workup

  1. customAcetone was removed under reduced pressure
  2. customThe residual solution was chromatographed on non-ionic adsorption resin "Diaion
  3. wash" (Trademark, maker: Mitsubishi Chemical Industries) eluting with water
  4. customThe desired fractions were collected

Sources & evidence

ORD record
ord-65f9aaabe5d44cb1ab3319cf595e762e
Source dataset
uspto-grants-1992_04
Patent number
US05104866

Reaction notes

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