Methanol → Methyl L-ornithine dihydrochloride

HRID 729063Notes

Reaction equation

HRID 729063 reaction equation
O.[NH2:2][C@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH2:6][NH2:7].S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[ClH:13].[CH3:15][O:9][C:8](=[O:10])[C@H:3]([CH2:4][CH2:5][CH2:6][NH2:7])[NH2:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 86745105HCID 86745105, compound

Product 1

HCID 14273060Methyl L-ornithine dihydrochloride

Procedure

To a solution of L-ornithine monohydrate (25 g) in methanol (200 ml) was added dropwise thionyl chloride (32.6 ml) under cooling and stirring and the reaction mixture was refluxed. After 6 hours the solvent was removed in vacuum and the residue was then treated with isopropyl ether (300 ml) and the precipitated solid filtered off to give L-ornithine methyl ester dihydrochloride (33.09 g) as a colorless powder (hygroscopic).

Workup

  1. temperatureunder cooling
  2. temperaturethe reaction mixture was refluxed
  3. customAfter 6 hours the solvent was removed in vacuum
  4. additionthe residue was then treated with isopropyl ether (300 ml)
  5. filtrationthe precipitated solid filtered off

Sources & evidence

ORD record
ord-99a6f5e5972d48de87f795284f498b52
Source dataset
uspto-grants-1991_09
Patent number
US05051509

Reaction notes

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