2-(4-Oxoazetidin-2-yl)ethenyl acetate → 2-(4-Oxoazetidin-2-yl)ethyl acetate

HRID 1154908Notes

Reaction equation

HRID 1154908 reaction equation
[C:1]([O:4][CH:5]=[CH:6][CH:7]1[NH:10][C:9](=[O:11])[CH2:8]1)(=[O:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[NH:10][C:9](=[O:11])[CH2:8]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 541779342-(4-Oxoazetidin-2-yl)ethenyl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 127692252-(4-Oxoazetidin-2-yl)ethyl acetateYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(2-acetoxyvinyl)-2-azetidinone (10.0 g, 0.065 mole) in 200 ml ethyl acetate containing 100 mg of 10% Pd/C is hydrogenated on a Parr shaker at 25° C. under 40 psi hydrogen for 15 minutes. The mixture is filtered through a bed of Supercel and washed with additional ethyl acetate. The combined filtrate is evaporated in vacuo to give 4-(2-acetoxyethyl)-2-azetidinone (10.0 g) as a crystalline solid. Recrystallization from ether affords white crystals: M.P. 44-7°; ir (CHCl3)μ5.66, 5.74; nmr (CDCl3)τ3.44 (broad s, 1, NH), 5.82 (m, 2, CH2OCOCH3), 6.29 (m, 1, C-4H), 6.87 (1/2 AB pattern further split in four by C-4H and NH, 1, Jgem =12.8 Hz, J=4.5H JNH =1.9 Hz, 7.38 (1/2 AB pattern further split in four by C-4H and NH, 1, Jgem =12.8 Hz, J=2.3 Hz, JNH =1.0 Hz), 7.93 and 8.02 (s on m, total 5, OCOCH3, and CH2CH2OCOCH3, respectively).

Workup

  1. filtrationThe mixture is filtered through a bed of Supercel
  2. washwashed with additional ethyl acetate
  3. customThe combined filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-755680da981c416686debcc55eb99b72
Source dataset
uspto-grants-1981_11
Patent number
US04298741

Reaction notes

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