Methacrylonitrile → gamma-Methyl-DL-ornithine

HRID 128721Notes

Reaction equation

C[CH:2]([CH2:8][CH2:9][NH2:10])[CH:3]([C:5]([OH:7])=[O:6])[NH2:4].[C:11](#N)C(C)=C.C(#N)/C=C/C>>[CH3:11][CH:8]([CH2:9][NH2:10])[CH2:2][CH:3]([C:5]([OH:7])=[O:6])[NH2:4]

Participants

Reactant 3

HCID 31368Methacrylonitrile

HCID 637921Crotononitrile

HCID 154816372,5-Diamino-3-methylpentanoic acid

Product 1

HCID 15481638gamma-Methyl-DL-ornithine

Procedure

γ-Methyl-DL-thiocitrulline (where R is H, R' is CH2 and R" is C(H)(CH3) and x is zero and Q is =S). This compound may be prepared by using y-methyl-DL-ornithine in place of L-ornithine in Example I. γ-Methyl-DL-ornithine is prepared as described above for β-methyl-DL-ornithine except methacrylonitrile is substituted for crotononitrile.

Workup

customThis compound may be prepared

Sources & evidence

ORD record: ord-cbc4affde1ff4c16af570c0f435d09e4
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464858

Reaction notes

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