2,5-Diamino-2-methylpentanoic acid hydrochloride → 2-Amino-5-[[1-(hydroxyimino)ethyl]amino]-2-methylpentanoic Acid, Dihydrochloride

HRID 1369180Notes

Reaction equation

HRID 1369180 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

Reactant 2

HCID 185191242,5-Diamino-2-methylpentanoic acid hydrochlorideHCID 57350373N-(2-Chloroethylidene)hydroxylamine

Product 1

HCID 1784657012-Amino-5-[[1-(hydroxyimino)ethyl]amino]-2-methylpentanoic Acid, Dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperatureat reflux
  2. washThe product is eluted from Dowex with 1N ammonium hydroxide
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-eb06487868184bf3ac67696b73a3afeb
Source dataset
uspto-grants-2003_06
Patent number
US06576780B1

Reaction notes

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