Hydrochloric Acid → cis-3-(2-Chloroacetyloxy-2-phenylacetamido)-2-oxoazetidine-4-carboxylic acid methyl ester

HRID 653303Notes

Reaction equation

HRID 653303 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH2:10])=[O:4].C(O[C:15](=[O:24])[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17])(=O)O.[Cl:25][CH2:26][C:27](Cl)=[O:28].Cl>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:15](=[O:24])[CH:16]([O:17][C:27](=[O:28])[CH2:26][Cl:25])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 53988551cis-3-Amino-4-methoxycarbonyl-2-oxoazetidineHCID 131714401Mandelic-carbonic anhydride

Product 1

HCID 86740437cis-3-(2-Chloroacetyloxy-2-phenylacetamido)-2-oxoazetidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 288 mg of cis-3-amino-2-oxoazetidine-4-carboxylic acid methyl ester in 2 ml of N,N-dimethylacetamide, which is stirred under ice-cooling beforehand, is added 534 mg of mandelic-carbonic anhydride, followed by stirring at room temperature for 30 minutes. The mixture is stirred beforehand under ice-cooling, to which is added dropwise 1.05 ml of chloroacetyl chloride, followed by stirring at room temperature for 3 hours. The reaction mixture is shaken with 100 ml of ethyl acetate and 20 ml of 1N-HCl, then the organic layer is separated. The organic layer is washed with a saturated aqueous solution of sodium chloride (30 ml×3), 20 ml of 1N-NaHCO3 aqueous solution and a saturated aqueous solution of sodium chloride (30 ml×3), successively, dried, and the solvent is evaporated under reduced pressure. The residue is purified by column-chromatography on silica-gel to afford cis-3-(2-chloroacetyloxy-2-phenylacetamido)-2-oxoazetidine-4-carboxylic acid methyl ester.

Workup

  1. temperaturecooling beforehand
  2. stirringThe mixture is stirred beforehand under ice-
  3. temperaturecooling, to which
  4. stirringby stirring at room temperature for 3 hours
  5. customthe organic layer is separated
  6. washThe organic layer is washed with a saturated aqueous solution of sodium chloride (30 ml×3), 20 ml of 1N-NaHCO3 aqueous solution
  7. dry with materiala saturated aqueous solution of sodium chloride (30 ml×3), successively, dried
  8. customthe solvent is evaporated under reduced pressure
  9. customThe residue is purified by column-chromatography on silica-gel

Sources & evidence

ORD record
ord-7de30cf59d5c45ff8ec341d8c2473619
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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