6-Hydroxypyridazine-3-carboxylic Acid → 1,4,5,6-Tetrahydro-6-oxo-3-pyridazinecarboxylic acid
Reaction equation
[2H][C@@:2]([C:11]([OH:13])=[O:12])([CH:4]([2H])[CH:5]([2H])[C:6](=[O:8])[NH2:7])[NH2:3].C(C1C=CC(=O)NN=1)(O)=O>>[C:11]([C:2]1[CH2:4][CH2:5][C:6](=[O:8])[NH:7][N:3]=1)([OH:13])=[O:12]Participants
Procedure
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.
Workup
- customwhich was obtained in a multi-step synthesis (see Blomquist, J. Org. Chem. 1966, 12, 4121-27)
Sources & evidence
- ORD record
- ord-db3b9bd1ce8248da809e502abd11cd18
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090585B2
Reaction notes
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