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

HRID 1533175Notes

Reaction equation

HRID 1533175 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-40d2cece45814e91a657e2591a0b30bd
Source dataset
uspto-grants-2001_03
Patent number
US06207708B1

Reaction notes

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