4-Methylmorpholine → 1-(1-Methoxycarbonyl-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone

HRID 1706530Notes

Reaction equation

HRID 1706530 reaction equation
[CH3:1][O:2][C:3]([CH:5]([NH:9][CH2:10][CH:11]([NH:15][C:16](=[O:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12](O)=[O:13])[CH:6]([CH3:8])[CH3:7])=[O:4].CN1CCOCC1.ClC1C=CC(S(ON2C3C=C(Cl)C=CC=3N=N2)(=O)=O)=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]([N:9]1[CH2:10][CH:11]([NH:15][C:16](=[O:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]1=[O:13])[CH:6]([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazoleHCID 543925623-(1-Methoxycarbonyl-2-methylpropylamino)-2-(2-phenylacetamido)propionic acid

Product 1

HCID 539575461-(1-Methoxycarbonyl-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinoneYield 1.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(1-Methoxycarbonyl-2-methylpropylamino)-2-(2-phenylacetamido)propionic acid (0.92 g) was dissolved in ethyl acetate (100 ml), and to the solution, there were added 4-methylmorpholine (0.66 g) and 1-(4-chlorobenzenesulfonyloxy)-6-chloro-1H-benzotriazole (1.11 g) under ice-cooling. The mixture was stirred at the same temperature for 18 hours and the insoluble materials were removed by filtration from the reaction mixture and ice-water (30 ml) was poured into the filtrate, whereafter the resultant mixture was stirred enough. The ethyl acetate layer was separated from the mixture, washed three times with an aqueous sodium bicarbonate and once with water, and then dried over magnesium sulfate. The solution was evaporated to dryness under reduced pressure to give a residue, which was subjected to column chromatography on silica gel (15 g). Elution was carried out with chloroform and the fractions containing a desired compound were collected. The solvent was removed by distillation from the eluate under reduced pressure to give 1-(1-methoxycarbonyl-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (10 mg), mp 105° to 107° C.

Workup

  1. temperaturecooling
  2. customthe insoluble materials were removed by filtration from the reaction mixture and ice-water (30 ml)
  3. additionwas poured into the filtrate, whereafter the resultant mixture
  4. stirringwas stirred enough
  5. customThe ethyl acetate layer was separated from the mixture
  6. washwashed three times with an aqueous sodium bicarbonate
  7. dry with materialonce with water, and then dried over magnesium sulfate
  8. customThe solution was evaporated to dryness under reduced pressure
  9. customto give a residue, which
  10. washElution
  11. additionthe fractions containing a desired compound
  12. customwere collected
  13. customThe solvent was removed by distillation from the eluate under reduced pressure

Sources & evidence

ORD record
ord-3efb43a21f2b43958bb36e412daaadf5
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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