HCID 86740458, compound → HCID 57113831, compound

HRID 621115Notes

Reaction equation

HRID 621115 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 icecooling 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. additionunder icecooling 27 mg of sodium hydrogen carbonate is added
  4. washwashed with ethyl acetate
  5. additionTo the aqueous layer is added 30 ml of Dowex 50W (H-form) resin
  6. stirringthe mixture is stirred for 1.5 hours
  7. filtrationThe resin is filtered off
  8. concentrationthe filtrate is concentrated under reduced pressure to about a half volume
  9. customThe residue is chromatographed on an Amberlite XAD-II (40 g) column
  10. washeluting with water

Sources & evidence

ORD record
ord-6a3b6bbae2a94a778ccf58b591904d11
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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