Acetic Acid → methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719276Notes

Reaction equation

Br[CH:2]1[C@@H:5]([CH2:6][CH:7]=[CH2:8])[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3]1=[O:17].C(O)(=O)C>C(Cl)Cl.C(OCC)(=O)C.[Zn]>[CH2:6]([C@H:5]1[N:4]([C:9](=[C:14]([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])[C:3](=[O:17])[CH2:2]1)[CH:7]=[CH2:8]

Participants

Conditions

Temperature: 5 °C

Procedure

Methyl 2-[(4R)-3-bromo-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (840 mg) was dissolved in methylene chloride (6 ml) and cooled to 5° C. To this cooled solution were added acetic acid (0.5 ml) and zinc powder (0.60 g), and the mixture was allowed to warm to room temperature. After stirring for 30 minutes, the reaction mixture was diluted with ethyl acetate (6 ml) and filtered through a pad of Celite. The filtrate was further diluted with ethyl acetate (50 ml) and washed successively with water, dilute sodium bicarbonate and brine. Drying over magnesium sulfate and evaporation left an oil, which was chromatographed on silica gel (20 g) eluting with a mixture of benzene and acetone (5:1) to give methyl 2-[(4R)-4-allyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoate (174 mg) as an oil.

Workup

temperatureto warm to room temperature
filtrationfiltered through a pad of Celite
additionThe filtrate was further diluted with ethyl acetate (50 ml)
washwashed successively with water, dilute sodium bicarbonate and brine
dry with materialDrying over magnesium sulfate and evaporation
waitleft an oil, which
customwas chromatographed on silica gel (20 g)
washeluting with a mixture of benzene and acetone (5:1)

Sources & evidence

ORD record: ord-e6fe6217a8d44d8987246e976942213a
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539152

Reaction notes

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