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Deuterium labelling of the GABA agonist thiomuscimol

✍ Scribed by Poul Jacobsen; Povl Krogsgaard-Larsen

Publisher
John Wiley and Sons
Year
1984
Tongue
French
Weight
300 KB
Volume
21
Category
Article
ISSN
0022-2135

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✦ Synopsis

Deuterium labelled thiomuscimol ( 6 ) was synthesized v i a zatalytic deuteration in strongly basic CZH302H-'H 0 (9:l) of 3-methoxy-4-bromo-5-(N-meth-oxycarbonyZaminomethy1) isothiazole ( 3 ) . ment of bromine by deuterium was accompanied by partial exchange of the side chain methylene protons for deuterium and by complete reesterification of the methoxycarbonyl group. Acid catalyzed deprotection of the reduction product 3-methoxy-4-['HI-5-

~N-[2H]methoxycarbonylamino[2H]methyl)isothiazole

( 5 ) gave 6 with only minor loss of deuterium from the ring and side chain.

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