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14C-labeling of a novel atypical β-adrenoceptor agonist, SM-11044

✍ Scribed by Motohiro Kurosawa; Hiroshi Kanamaru; Kazuhiko Nishioka

Publisher
John Wiley and Sons
Year
1996
Tongue
French
Weight
637 KB
Volume
38
Category
Article
ISSN
0022-2135

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✦ Synopsis

2S,3R)-2-[3-(4-Fluorophenyl)]propylamino-3-(3,4-di hydroxyphenyl)-3-hydroxypropionic acid pyrrolidine amide hydrobromide (SM-11044) was labeled with carbon-14 for use in mammalian metabolic studies. The synthesis was achieved according to the scheme shown in Fig. 5. Grignard reaction of 3,4-methylenedioxyphenylmagnesium bromide with ["Clcarbon dioxide liberated from barium ("Clcarbonate (6) gave the acid (5). Reduction of 5 with lithium aluminum hydride followed by oxidation of the resulting benzyl alcohol (11) with chromium oxide-pyridine complex afforded the aldehyde (a). Condensation of 9 with the optically active (0oxazolidinone (m yielded the alcohol (w. Catalytic hydrogenation of 12 and subsequent hydrolysis produced the optically active p-hydroxyaamino acid (2), which was treated with N-carbomethoxyphthalimide to give the hydroxy acid (la).

Reaction of J3 with pivaloyl chloride gave the corresponding mixed anhydride, which was allowed to react with pyrrolidine to provide the amide (M). Deprotection of 14 with hydrazine hydrate afforded the hydroxyamide (E). Condensation of I5 with the aldehyde (Ls) and subsequent reduction of the resulting imine with sodium cyanoborohydride produced the fluoride (Iz). Cleavage of the methylenedioxy group of Lz gave the free base of 1 , which was treated with hydrobromic acid to afford 1. The overall yield was 11.1%from6.

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