Sodium Bicarbonate → HCID 70551266, compound

HRID 978860Notes

Reaction equation

HRID 978860 reaction equation
C([O:8][C:9]([CH:11]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]([NH:14][C@H:15]1[C@@H:18]([C:19]([O:21][CH3:22])=[O:20])[N:17]([S:23]([O-:26])(=[O:25])=[O:24])[C:16]1=[O:27])=[O:13])=[O:10])C1C=CC=CC=1.[Na+].C(=O)([O-])O.[Na+]>[Pd].C(O)C>[C:9]([CH:11]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:12]([NH:14][C@H:15]1[C@@H:18]([C:19]([O:21][CH3:22])=[O:20])[N:17]([S:23]([OH:26])(=[O:25])=[O:24])[C:16]1=[O:27])=[O:13])([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70390990HCID 70390990, compound

Product 1

HCID 70551266HCID 70551266, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 6 ml of 80% ethanol are added 106 mg of sodium cis-3-(2-benzyloxycarbonyl-2-phenylacetamido)-4-methoxycarbonyl-2-oxoazetidine-1-sulfonate, 106 mg of 5% palladium-on-carbon and 16.8 mg of sodium hydrogen carbonate, and the mixture is vigorously stirred under hydrogen atmosphere for 3.5 hours at ambient temperature under atmospheric pressure. The reaction mixture is subjected to filtration, and the filtrate is concentrated under reduced pressure. The concentrate is purified by column chromatography on Amberlite XAD-II, followed by lyophilization to give cis-3-(2-carboxy-2-phenylacetamido)-4-methoxycarbonyl-1-sulfo-2-oxoazetidine.disodium salt as a mixture of diastereoisomers.

Workup

  1. filtrationThe reaction mixture is subjected to filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe concentrate is purified by column chromatography on Amberlite XAD-II

Sources & evidence

ORD record
ord-7cba601f794b4b229e3bfd5dedc24a12
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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