L-Lysine → 2-Hydroxybutanedioic acid--lysine (1/1)

HRID 904789Notes

Reaction equation

HRID 904789 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[C:11]([OH:19])(=[O:18])[C@H:12]([CH2:14][C:15]([OH:17])=[O:16])[OH:13]>>[C:11]([OH:19])(=[O:18])[C@H:12]([CH2:14][C:15]([OH:17])=[O:16])[OH:13].[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

3

Reactant 2

HCID 5962L-LysineHCID 222656L-Malic Acid

Product 1

HCID 717498192-Hydroxybutanedioic acid--lysine (1/1)

Procedure

To an aqueous solution of free L-lysine (200 ml, content of L-lysine: 0.45 mole) is gradually added with stirring L-malic acid (30.16 g, 1/2 mole per 1 mole of L-ysine). The reaction mixture is concentrated under reduced pressure to give a 50% aqueous solution of neutral L-lysine L-malate (liquid volume: about 170 ml). To the resulting solution is gradually added with stirring methanol (200 ml) to precipitate crystals. To a separate vessel containing methanol (470 ml) is added with stirring the above-obtained mixture, and the mixture is stirred at room temperature for about 4 hours. The precipitated crystals are collected by filtration and washed with methanol and air-dried at 40° C. overnight to give a neutral L-lysine L-malate monohydrate (91.9 g, yield: 92.5%) as colorless needle or prismatic crystals. m.p. 216° C. (decomp.)

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ba1c10aeb42749e5b4d8d7a09a99e08e
Source dataset
uspto-grants-1983_12
Patent number
US04420432

Reaction notes

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