HCID 86740458, compound → HCID 57113831, compound

HRID 653281Notes

Reaction equation

HRID 653281 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][C:25]([CH3:40])([C:27]([O:29]CC2C=CC([N+]([O-])=O)=CC=2)=[O:28])[CH3:26])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15](=[O:17])[NH2:16])[N:13]([S:18]([O-:21])(=[O:20])=[O:19])[C:12]2=[O:22])=[O:9])[N:6]=1.[Na+].[H][H]>O.[Pd]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][C:25]([CH3:40])([C:27]([OH:29])=[O:28])[CH3:26])[C:8]([NH:10][C@H:11]2[C@@H:14]([C:15](=[O:17])[NH2:16])[N:13]([S:18]([OH:21])(=[O:20])=[O:19])[C:12]2=[O:22])=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 86740458HCID 86740458, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57113831HCID 57113831, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In 10 ml of water is dissolved 200 mg of sodium cis-3-{2-(2-amino-4-thiazolyl)-2-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethyloxyimino]acetamido}-4-carbamoyl-2-oxoazetidine-1-sulfonate (syn-isomer) as obtained in Example 132C, followed by addition of 200 mg of 10% palladium-on-carbon. The mixture is stirred in a hydrogen atmosphere at room temperature for one hour. The catalyst is filtered off, and under ice-cooling 27 mg of sodium hydrogen carbonate is added. The mixture is stirred for 5 minutes and washed with ethyl acetate. To the aqueous layer is added 30 ml of Dowex 50W (H-form) resin, and the mixture is stirred for 1.5 hours. The resin is filtered off and the filtrate is concentrated under reduced pressure to about a half volume thereof. The residue is chromatographed on an Amberlite XAD-II (40 g) column, eluting with water and then 15% ethanol. The fractions including the desired product are combined and lyophilized to give cis-3-[2-(2-amino-4-thiazolyl)-2-(1-methyl-1-carboxyethyloxyimino)acetamido]-4-carbamoyl-2-oxoazetidine-1-sulfonic acid (syn-isomer).

Workup

  1. customas obtained in Example 132C
  2. filtrationThe catalyst is filtered off
  3. temperatureunder ice-cooling 27 mg of sodium hydrogen carbonate
  4. additionis added
  5. washwashed with ethyl acetate
  6. additionTo the aqueous layer is added 30 ml of Dowex 50W (H-form) resin
  7. stirringthe mixture is stirred for 1.5 hours
  8. filtrationThe resin is filtered off
  9. concentrationthe filtrate is concentrated under reduced pressure to about a half volume
  10. customThe residue is chromatographed on an Amberlite XAD-II (40 g) column
  11. washeluting with water

Sources & evidence

ORD record
ord-6a5bba7d042347bd9c6db5b53e8434a0
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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