L-Lysine monohydrochloride → L-Lysine

HRID 1381154Notes

Reaction equation

HRID 1381154 reaction equation
ClC1C=CC=C(SC(C2C=CC(OC)=CC=2)C([N+]([O-])=O)(O)C(O)=O)C=1.Cl.[NH2:27][C@H:28]([C:34]([OH:36])=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][NH2:33].[K]>CO>[NH2:27][C@H:28]([C:34]([OH:36])=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][NH2:33]

Participants

5

Reactant 3

HCID 69568L-Lysine monohydrochlorideHCID 5462222PotassiumHCID 131714645HCID 131714645, compound

Product 1

HCID 5962L-Lysine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.04 g of (±)-threo-3-(5-chloro-2-nitrophenylthio-2-hydroxy-3-(4-methoxyphenyl)propionic acid are dissolved in 110 ml of methanol, and 3.85 g of L-lysine.hydrochloride are added thereto. 21 ml of a solution of 1N potassium hydroxidemethanol are added to the mixture under ice-cooling, and the mixture is allowed to stand at room temperature. Crystalline precipitates are collected by filtration (the mother liquor is hereinafter referred to as "mother liquor (I)"). The crystals (10.56 g) are recrystallized three times repeatedly from a mixture of dimethylformamide and water (1:1) (the mother liquors are hereinafter referred to as "mother liquor (II)"). 4.29 g of (+)-threo-3-(5-chloro-2-nitrophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propionic acid.L-lysine salt are obtained.

Workup

  1. temperaturecooling
  2. customto stand at room temperature
  3. customCrystalline precipitates
  4. filtrationare collected by filtration (the mother liquor
  5. customThe crystals (10.56 g) are recrystallized three times
  6. additionrepeatedly from a mixture of dimethylformamide and water (1:1) (the mother liquors

Sources & evidence

ORD record
ord-f3d08fff73be42b9a823ae3b499b9c93
Source dataset
uspto-grants-1986_04
Patent number
US04585768

Reaction notes

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