Sodium Bicarbonate → HCID 131714400, compound

HRID 465222Notes

Reaction equation

HRID 465222 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][C:26]([CH3:41])([C:28]([O:30]CC2C=CC([N+]([O-])=O)=CC=2)=[O:29])[CH3:27])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([O-:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1.[Na+:42].[H][H].C(=O)([O-])O.[Na+]>O.O1CCCC1.[Pd]>[Na+:42].[Na+:42].[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][C:26]([CH3:41])([C:28]([OH:30])=[O:29])[CH3:27])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([O-:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1.[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:24][O:25][C:26]([C:28]([OH:30])=[O:29])([CH3:27])[CH3:41])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15]([O:17][CH3:18])=[O:16])[N:13]([S:19]([O-:22])(=[O:21])=[O:20])[C:12]2=[O:23])=[O:9])[N:6]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 86740441Sodium cis-3-{2-(2-amino-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-methoxycarbonyl-2-oxoazetidine-1-sulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 131714400HCID 131714400, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 25 ml of water and 25 ml of tetrahydrofuran is dissolved 500 mg of sodium cis-3-{2-(2-amino-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate (syn-isomer), followed by addition of 500 mg of 10% palladium-on-carbon. The mixture is stirred in a hydrogen atmosphere at room temperature for one hour. After addition of 25 ml of an aqueous solution of sodium hydrogen carbonate (62 mg), the catalyst is filtered off and the filtrate is washed with ethyl acetate and concentrated under reduced pressure. The residue is chromatographed on an Amberlite XAD-II column and lyophilized to give cis-3-[2-(2-amino-4-thiazolyl)-2-(1-methyl-1-carboxyethyloxyimino)acetamido]-4-methoxycarbonyl-2-oxoazetidine-1-sulfonic acid disodium salt (syn-isomer).

Workup

  1. filtrationthe catalyst is filtered off
  2. washthe filtrate is washed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is chromatographed on an Amberlite XAD-II column

Sources & evidence

ORD record
ord-c178678bad2047e28d6583ca978c5fd1
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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