6-Hydroxypyridazine-3-carboxylic Acid → 1,4,5,6-Tetrahydro-6-oxo-3-pyridazinecarboxylic acid

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A number of deuterated glutamines (Compound C) have previously been made including 2,3,4-trideutero-glutamine (i.e., R2=D, R4=D, and 3′-D is present), which was made via the deuterium reduction of 6-carboxy-3(2H)-pyridazone (see Stogniew, J. Labelled Compounds and Radiopharmaceuticals 1981, 18(6), 897-903), and 2,2,3,3,4 pentadeutero-glutamine (i.e., R2-R5=D and 3′-D is present), which was obtained in a multi-step synthesis (see Blomquist, J. Org. Chem. 1966, 12, 4121-27). Stogniew also notes that the 5-mono-deutero-glutamine could be obtained through deuterium reduction of 4,5-dihydro-6-carboxy-3(2H)-pyridazone. D1 (1-D) and D4 (2,2,3,3-D) cyclopropane carboxylic acids are commercially available. Cyclopropane-D5-carbonyl chloride is also commercially available.

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