HCID 20243605, compound → HCID 53776457, compound

HRID 1706529Notes

Reaction equation

HRID 1706529 reaction equation
[CH3:1][O:2][C:3]([CH:5]([N:12]1[CH:15](SC)[CH:14]([NH:18][C:19](=[O:27])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]1=[O:28])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4]>O1CCOCC1.[Ni]>[CH3:1][O:2][C:3]([CH:5]([N:12]1[CH2:15][CH:14]([NH:18][C:19](=[O:27])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]1=[O:28])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 1

HCID 20243605HCID 20243605, compound

Product 1

HCID 53776457HCID 53776457, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

1-(α-Methoxycarbonylbenzyl)-4-methylthio-3-(2-phenylacetamido)-2-azetidinone (mixture of two trans isomers at the third and fourth positions of the azetidine ring) (0.50 g) was dissolved in dried dioxane (10 ml), and to the solution, there was added an dioxane solution (10 ml) containing Raney nickel (5 ml). The mixture was stirred at 60° C. for 2 hours. Raney nickel was removed by filtration to give a filtrate, which was evaporated to dryness under reduced pressure. The residue obtained was subjected to column chromatography on silica gel (10 g) and elution was carried out with chloroform. The fractions containing a desired compound were collected and the solvent was distilled off from the solution under reduced pressure to give 1-(α-methoxycarbonylbenzyl)-3-(2-phenylacetamido)-2-azetidinone (mixture of two isomers at the third position of the azetidine ring, 320 mg). Additionally this mixture was subjected to column chromatography on silica gel and elution was carried out with chloroform. The eluate was treated in a conventional manner to give each isomer a: 180 mg and b: 140 mg of the above compound.

Workup

  1. customRaney nickel was removed by filtration
  2. customto give a filtrate, which
  3. customwas evaporated to dryness under reduced pressure
  4. customThe residue obtained
  5. washwas subjected to column chromatography on silica gel (10 g) and elution
  6. additionThe fractions containing a desired compound
  7. customwere collected
  8. distillationthe solvent was distilled off from the solution under reduced pressure

Sources & evidence

ORD record
ord-da2bc82697fe4ff8932883916527c1f9
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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