Inversion of the 3 .alpha.-amino group attached to the .beta.-la

Details Inversion of the 3 .alpha.-amino group attached to the .beta.-la Inversion of the 3 .alpha.-amino group attached to the .beta.-la

1980-03-28

1982-08-03

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544 90, C07D70508, C07D49804, C07B 2900

Patent

active

043426859

ABSTRACT:
A process for preparing 3.beta.-amino-4.beta.-substituted-2-azetidinones, which comprises condensing a 3.alpha.-amino-4.beta.-substituted-2-azetidinone with a trihalogenoacetaldehyde or the reactive derivative thereof to give a 3.alpha.-(2,2,2-trihalogenoethylidene)amino-4.beta.-substituted-2-azetidin ones, treating the latter with a base to give a 3-(2,2-dihalogenovinyl)imino-4.beta.-substituted-2-azetidinone, reducing the latter with a metal hydride to give a 3.beta.-(2-halogenovinyl)amino-4.beta.-substituted-2-azetidinone, and hydrolyzing the latter to give the objective compound.

REFERENCES:
Vlietinck et al., Tet. Letters 1972, 285-287.
Firestone et al., J. Org. Chem. 39, 437-440 (1974).
Miyadera et al., Chem. Abs. 90, 186975h (1978).
Hiraoka et al., Chem. Abs. 90, 204118n (1978).

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