Acetate → HCID 86740420, compound

HRID 465214Notes

Reaction equation

HRID 465214 reaction equation
C([O-])(=O)C.C([O-])(=O)C.[C:9]([O:12][C@@H:13]1[N:16]([S:17]([OH:20])(=[O:19])=[O:18])[C:15](=[O:21])[C@H:14]1[NH2:22])(=[O:11])[CH3:10].[Na+:23].[C:24]1([CH2:30][C:31](Cl)=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>C1COCC1.O>[C:9]([O:12][C@@H:13]1[N:16]([S:17]([O-:20])(=[O:19])=[O:18])[C:15](=[O:21])[C@H:14]1[NH:22][C:31](=[O:32])[CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:11])[CH3:10].[Na+:23]

Participants

7

Reactant 4

HCID 175AcetateHCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 86740421HCID 86740421, compound

Product 1

HCID 86740420HCID 86740420, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.61 g of acetate of sodium (3S,4R)-4-acetoxy-3-amino-2-oxoazetidine-1-sulfonate obtained in Example 21B in 20 ml of a mixture of water and THF(1:1) is added under ice-cooling 0.61 of g phenylacetyl chloride while keeping the pH of the reaction mixture at pH 7.0-7.5 by use of sodium hydrogen carbonate. The stirring is continued for 1.5 hours at the same temperature. THF is removed by evaporation under reduced pressure. The residue is purified on an XAD-II (Rohm and Haas Co.) column chromatography to give 0.42 g of sodium (3S,4S)-4-acetoxy-3-phenylacetamido-2-oxoazetidine-1-sulfonate. The IR spectrum and NMR data of this compound are in agreement with those of the compound obtained in Example 19B.

Workup

  1. customTHF is removed by evaporation under reduced pressure
  2. customThe residue is purified on an XAD-II (Rohm and Haas Co.) column chromatography

Sources & evidence

ORD record
ord-1ad03de9cfab405dbe0a51364e42ad23
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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