L-Lysine → L-Lysine

HRID 583541Notes

Reaction equation

HRID 583541 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].N([O-])=[O:12].[Na+]>O.C([O-])([O-])=O.O.O.[Cu].[Cu+2]>[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[NH2:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][OH:12])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 5962L-LysineHCID 23668193Sodium Nitrite

Product 2

HCID 5962L-LysineYield 60%HCID 97725epsilon-HydroxynorleucineYield 30%

Reagents, catalysts & solvents 2

HCID 10922056HCID 10922056, compoundCatalystHCID 962WaterSolvent2×

Procedure

A suspension of L-lysine (0.931 g, 5.1 mmol) and CuCO3.Cu(OH)2 (1.24 g, 5.6 mmol) in water (15 ml) was heated under reflux for 5 minutes then cooled and filtered. The pH of the filtrate was adjusted to 4 with 2M H2SO4. A solution of sodium nitrite (0.70 g, 10 mmol) in water (5 ml) was added dropwise over 10 minutes and the mixture was strirred at 24° C. for 6 hours. Chelex 100 resin (40 g) was added to effect decomplexation. The resulting suspension was then filtered to give a solution of L-lysine (60%) and (S)-2-amino-6-hydroxyhexanoic acid 2 (30%). ##STR2##

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 minutes
  3. temperaturethen cooled
  4. filtrationfiltered
  5. filtrationThe resulting suspension was then filtered

Sources & evidence

ORD record
ord-3d6da3c6495941b084744d23ebe35ff1
Source dataset
uspto-grants-1999_07
Patent number
US05929242

Reaction notes

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