2,5-Diamino-2-methylpentanoic acid hydrochloride → 2-Amino-5-[[1-(hydroxyimino)ethyl]amino]-2-methylpentanoic Acid, Dihydrochloride
Reaction equation
[ClH:1].[CH3:2][C:3]([C:9]([OH:11])=[O:10])([CH2:5][CH2:6][CH2:7][NH2:8])[NH2:4].[Cl:12][CH2:13][CH:14]=[N:15][OH:16]>O>[ClH:12].[ClH:1].[NH2:4][C:3]([CH3:2])([CH2:5][CH2:6][CH2:7][NH:8][C:14](=[N:15][OH:16])[CH3:13])[C:9]([OH:11])=[O:10]Participants
4
Procedure
α-Methyl-D,L-ornithine hydrochloride is protected as a copper complex via reaction with cupric carbonate in water at reflux. This protected amino acid is then reacted with chloroacetaldoxime as in Example 1. The product is eluted from Dowex with 1N ammonium hydroxide. Concentration in vacuo, followed by acidification with hydrochloric acid affords the title compound.