Hydrochloric Acid → HCID 86740479, compound

HRID 653314Notes

Reaction equation

HRID 653314 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:31][O:32][CH3:33])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][NH:20][C:21]([O:23][CH2:24][CH2:25]S(C)(=O)=O)=[O:22])[NH:17][C:16]2=[O:30])=[O:13])[N:10]=1)=[O:4].[OH-:34].[Na+].Cl.[CH2:37](O)[CH3:38]>CN(C)C=O>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:31][O:32][CH3:33])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]3[CH:38]=[CH:37][C:11]([N+:31]([O-:32])=[O:34])=[CH:9][CH:8]=3)=[O:22])[NH:17][C:16]2=[O:30])=[O:13])[N:10]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86740480HCID 86740480, compound

Product 1

HCID 86740479HCID 86740479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a mixture of 25 ml of ethanol and 5 ml of N,N-dimethylformamide is suspended 525 mg of cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-(2-methylsulfonylethoxycarbonylaminomethyl)-2-oxoazetidine (syn-isomer) as obtained in Reference Example 119C, followed by addition of 5 ml of ethanolic sodium hydroxide (0.5N). The mixture is stirred at room temperature for 20 minutes, after which 2.5 ml of 1N HCl is added. The ethanol is distilled off under reduced pressure and the residue is dissolved in a mixture of 8 ml of water and 10 ml of tetrahydrofuran. Under ice-cooling and stirring, 185 mg of sodium hydrogen carbonate is added, followed by dropwise addition of a solution of 432 mg of p-nitrobenzyl chloroformate in 10 ml of tetrahydrofuran over 50 minutes. The mixture is stirred under ice-cooling for 20 minutes and to this reaction mixture are added 10 ml of water and 20 ml of ethyl acetate. The mixture is shaken well, whereupon the organic layer separates out. The aqueous layer is extracted with ethyl acetate and this ethyl acetate extract and the above organic layer are combined, washed with aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is crystallized from ethyl acetate and recovered by filtration to give cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-(p-nitrobenzyloxycarbonylaminomethyl)-2-oxoazetidine (syn-isomer), m.p. 235°-245° C. (decomp.).

Workup

  1. customas obtained in Reference Example 119C
  2. distillationThe ethanol is distilled off under reduced pressure
  3. dissolutionthe residue is dissolved in a mixture of 8 ml of water and 10 ml of tetrahydrofuran
  4. temperatureUnder ice-cooling
  5. stirringstirring
  6. addition185 mg of sodium hydrogen carbonate is added
  7. additionfollowed by dropwise addition of a solution of 432 mg of p-nitrobenzyl chloroformate in 10 ml of tetrahydrofuran over 50 minutes
  8. stirringThe mixture is stirred under ice-
  9. temperaturecooling for 20 minutes and to this reaction mixture
  10. additionare added 10 ml of water and 20 ml of ethyl acetate
  11. stirringThe mixture is shaken well, whereupon the organic layer
  12. extractionThe aqueous layer is extracted with ethyl acetate
  13. extractionthis ethyl acetate extract
  14. washwashed with aqueous sodium chloride
  15. dry with materialdried over anhydrous magnesium sulfate
  16. distillationThe solvent is then distilled off under reduced pressure
  17. customthe residue is crystallized from ethyl acetate
  18. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-fca94290ec554074bc578fde5036f31c
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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