Isotopically labelled fatty acids

Details Isotopically labelled fatty acids Isotopically labelled fatty acids

C - Chemistry, Metallurgy

07

D

260/506.9

C07D 309/12 (2006.01)

Patent

CA 1078865

TITLE OF THE INVENTION Isotopically Labelled Fatty Acids ABSTRACT OF THE DISCLOSURE The present invention relates to a process for the preparation of specifically labelled fatty acids and particularly to certain tetradeuterated or trideuterated palmitic acids. The novel compounds of the present inven- tion--specifically labelled palmitic acids including pal- mitic-5,5,6,6-d4 acid, palmitic-7,7,8,8-d4 acid, palmitic- 16,16,16-d3 acid, and palmitic-11,11,12,12-d4 acid--are prepared by a synthetic scheme which involves a combina- tion of steps, including the alkylation of an intermediate containing a terminal acetylenic moiety and subsequently hydrogenating or deuterogenating the acetylenic bond in the presence of the soluble hydrogenation catalyst, tris- (triphenylphosphoro)rhodium chloride, to produce the corresponding saturated compound in which the acetylenic bond is saturated with either hydrogen or deuterium. Sub- sequent synthetic steps are utilized to convert functional substituents by known reaction steps to a carboxylic acid substituent, thus producing the novel compounds of the present invention.

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