Dimethylformamide → methyl 2-[(4R)-4-(2-oxopropyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719278Notes

Reaction equation

HRID 1719278 reaction equation
[CH2:1]([C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[CH2:5]1)[CH:2]=[CH2:3].CN(C)C=[O:20]>O.C(OCC)(=O)C.[Pd](Cl)Cl>[O:20]=[C:2]([CH3:3])[CH2:1][C@H:4]1[N:7]([C:8](=[C:13]([CH3:15])[CH3:14])[C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:16])[CH2:5]1

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 54326273methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

Product 1

HCID 54205607methyl 2-[(4R)-4-(2-oxopropyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-[(4R)-4-allyl-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (100 mg), palladium chloride (16 mg) and cuprous chloride (44 mg) in a mixture of dimethylformamide (1 ml) and water (0.12 ml) was stirred under an oxygen atmosphere for 3.5 hours. The reaction mixture was diluted with ethyl acetate (20 ml), and filtered. The filtrate was washed with water and brine. The combined aqueous layer was extracted with ethyl acetate (10 ml×2) and the extract was washed with brine. The organic layers were combined, and dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed on silica gel (1 g) eluting with methylene chloride and acetone (100:2-100:5) to give methyl 2-[(4R)-4-(2-oxopropyl)-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (89 mg as an oil.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water and brine
  3. extractionThe combined aqueous layer was extracted with ethyl acetate (10 ml×2)
  4. washthe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe oily residue was chromatographed on silica gel (1 g)
  8. washeluting with methylene chloride and acetone (100:2-100:5)

Sources & evidence

ORD record
ord-b985f6da9b0b48c8829607bd8ecfc1ca
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

Loading…