Potassium Carbonate → HCID 13848562, compound

HRID 2051698Notes

Reaction equation

HRID 2051698 reaction equation
[N:1]([CH:4]1[CH:7](Cl)[N:6]([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:12][CH3:13])=[O:11])[C:5]1=[O:20])=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+].[CH3:27][C:28]1[S:32][C:31]([SH:33])=[N:30][N:29]=1>C(Cl)Cl>[N:1]([CH:4]1[CH:7]([S:33][C:31]2[S:32][C:28]([CH3:27])=[N:29][N:30]=2)[N:6]([CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:12][CH3:13])=[O:11])[C:5]1=[O:20])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20243626HCID 20243626, compoundHCID 178434161HCID 178434161, compound

Product 1

HCID 13848562HCID 13848562, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3-azido-4-chloro-2-oxo-1-azetidinyl)-2-phenylacetate (two trans and two cis isomers) (4.0 g.) was dissolved in dried methylene chloride (50 ml.), and to the solution were added anhydrous potassium carbonate (1.13 g.) and 5-methyl-1,3,4-thiadiazole-2-thiol (2.10 g.). The mixture was stirred at room temperature for 8 hrs, poured into icewater and then extracted with ether. The extract was washed with 1% aqueous potassium carbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off from the solution under reduced pressure, and the residue (4.05 g.) was subjected to column chromatography on silica gel (160 g.). The elution was conducted with chloroform and the fractions containing the object compound were collected. The solvent was distilled off from the solution under reduced pressure to give methyl 2-[3-azido-4-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxo-1-azetidinyl]-2-phenylacetate (two trans and two cis isomers) (2.81 g.).

Workup

  1. additionpoured into icewater
  2. extractionextracted with ether
  3. washThe extract was washed with 1% aqueous potassium carbonate and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off from the solution under reduced pressure
  6. washThe elution
  7. additionthe fractions containing the object compound
  8. customwere collected
  9. distillationThe solvent was distilled off from the solution under reduced pressure

Sources & evidence

ORD record
ord-aed5534059fd46879ba20eee08cf612d
Source dataset
uspto-grants-1980_01
Patent number
US04181800

Reaction notes

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