Sodium Bicarbonate → HCID 86740438, compound

HRID 653274Notes

Reaction equation

HRID 653274 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH3:35])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17]CC3C=CC([N+]([O-])=O)=CC=3)=[O:16])[N:13]([S:28]([O-:31])(=[O:30])=[O:29])[C:12]2=[O:32])=[O:9])[N:6]=1.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.O.[Pd]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH3:35])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([OH:17])=[O:16])[N:13]([S:28]([OH:31])(=[O:29])=[O:30])[C:12]2=[O:32])=[O:9])[N:6]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 86740439HCID 86740439, compound

Product 1

HCID 86740438HCID 86740438, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 10 ml of tetrahydrofuran and 10 ml of water is dissolved 155 mg of sodium cis-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-(4-nitrobenzyloxycarbonyl)-2-oxoazetidine-1-sulfonate (syn-isomer). To the solution is added 145 mg of 10% palladium-on-carbon, and the mixture is subjected to catalytic reduction at ambient temperature under normal pressure with stirring. Three hours later, 10 ml of an aqueous solution of 25 mg of sodium hydrogen carbonate is added to the reaction mixture. The catalyst is removed by filtration, and the filtrate is washed with ethyl acetate, and concentrated under reduced pressure. The concentrate is purified by column chromatography on Amberlite XAD-II, followed by lyophilization to give cis-3-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-4-carboxy-1-sulfo-2-oxoazetidine.disodium salt (syn-isomer).

Workup

  1. customis subjected to catalytic reduction at ambient temperature under normal pressure
  2. customThe catalyst is removed by filtration
  3. washthe filtrate is washed with ethyl acetate
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate is purified by column chromatography on Amberlite XAD-II

Sources & evidence

ORD record
ord-acd91232ce0f466bacd3683e3d9191e4
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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