L-(-)-Ornithine → HCID 131713240, compound

HRID 904786Notes

Reaction equation

HRID 904786 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][NH2:6].[C:10]([OH:18])(=[O:17])[C@H:11]([CH2:13][C:14]([OH:16])=[O:15])[OH:12]>>[OH2:8].[OH2:12].[C:10]([OH:18])(=[O:17])[C@H:11]([CH2:13][C:14]([OH:16])=[O:15])[OH:12].[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][CH2:5][NH2:6]

Participants

3

Reactant 2

HCID 6262L-(-)-OrnithineHCID 222656L-Malic Acid

Product 1

HCID 131713240HCID 131713240, compoundYield 309%

Procedure

To an aqueous solution of free L-ornithine (400 ml, content of L-ornithine: 1.167 mole) is gradually added with stirring L-malic acid (78.29 g, 1/2 mole per 1 mole of L-ornithine). The reaction mixture is concentrated under reduced pressure until the total amount of the mixture becomes 500 g. To the resulting aqueous solution is added with stirring methanol (300 ml), by which a little amount of crystals is precipitated. To the mixture is further added methanol (each 100 ml) five times at an interval of 10 minutes. The mixture is allowed to stand at room temperature to crystallize out the salt well, and the precipitated crystals are separated by filtration. The crystals are washed with a 90% aqueous methanol solution and are air-dried at 60° C. overnight to give neutral L-ornithine L-malate dihydrate (233.5 g, yield: 92.1%) as colorless platy crystal. m.p. 136° C. (decomp.)

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure until the total amount of the mixture
  2. additionTo the resulting aqueous solution is added with stirring methanol (300 ml), by which a little amount of crystals
  3. customis precipitated
  4. customat an interval of 10 minutes
  5. customto stand at room temperature
  6. customto crystallize out the salt well
  7. customthe precipitated crystals are separated by filtration
  8. washThe crystals are washed with a 90% aqueous methanol solution
  9. customare air-dried at 60° C. overnight

Sources & evidence

ORD record
ord-53fb28162d4740d3898d279d63bde1b4
Source dataset
uspto-grants-1983_12
Patent number
US04420432

Reaction notes

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