Phosphoric Acid → Sodium 3-phenylacetamido-2-oxoazetidine-1-sulfonate

HRID 620975Notes

Reaction equation

HRID 620975 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([S:6]([OH:9])(=[O:8])=[O:7])[C:3]1=[O:10].[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])O.[Na+:25].P(=O)(O)(O)O>O.O1CCCC1>[C:11]1([CH2:17][C:18]([NH:1][CH:2]2[CH2:5][N:4]([S:6]([O-:9])(=[O:8])=[O:7])[C:3]2=[O:10])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+:25]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 130190953-Amino-2-oxoazetidine-1-sulfonic acid

Product 1

HCID 23695024Sodium 3-phenylacetamido-2-oxoazetidine-1-sulfonateYield 45.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 1 ml of water is dissolved 50 mg of the above 3-amino 2-oxoazetidine-1-sulfonic acid, followed by addition of a solution of 69 mg phenylacetyl chloride in 1 ml tetrahydrofuran and 101 mg of sodium hydrogen carbonate in alternate portions with ice-cooling and stirring. After stirring at room temperature for 30 minutes, the mixture is adjusted to pH 5.8 with phosphoric acid. The tetrahydrofuran is then distilled off under reduced pressure. The water layer is washed with ethyl acetate and purified by XAD-II chromatography, whereby 42 mg of sodium 3-phenylacetamido-2-oxoazetidine-1-sulfonate is obtained.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for 30 minutes
  3. distillationThe tetrahydrofuran is then distilled off under reduced pressure
  4. washThe water layer is washed with ethyl acetate
  5. custompurified by XAD-II chromatography

Sources & evidence

ORD record
ord-11a06545a1fa470092ef476ee16deb90
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

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