Methanol → L-Lysine

HRID 1586771Notes

Reaction equation

HRID 1586771 reaction equation
O.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].C([O-])([O-])=O.[Na+].[Na+].CO>O>[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8]

Participants

5

Procedure

5.61 g (0.034 mole) of L-lysine monohydrate was dissolved in 150 cm3 of distilled water in a round-bottom flask equipped with magnetic stirrer. The solution was heated to 80° C. and, with continuous stirring, Cu(OH)2.CuCO3.xH2O was added in small portions until it appeared to be dissolved. The possible excess of Cu(OH)2.CuCO3.xH2O, remained after stirring for 15 minutes, was filtered out. The solution was cooled to room temperature with continued stirring and 1.8 g (0.017 mole) of Na2CO3 then 12.2 g (0.034 mole) of the mixture of fatty acyl chlorides prepared as in Example 4 were added dropwise. After 1-hour stirring, the acylated copper complex precipitate was filtered then washed once with methanol and several times with water until a colorless was liquor had been obtained. In a round-bottom flask, 200 cm3 of methanol was added to the copper complex and the complex was decomposed by bubbling gaseous H2S through the mixture.

Workup

  1. customequipped with magnetic stirrer
  2. additionxH2O was added in small portions until it
  3. dissolutionto be dissolved
  4. filtrationwas filtered out
  5. stirringwith continued stirring
  6. additionwere added dropwise
  7. stirringAfter 1-hour stirring
  8. filtrationthe acylated copper complex precipitate was filtered
  9. washthen washed once with methanol and several times with water until
  10. customhad been obtained
  11. customby bubbling gaseous H2S through the mixture

Sources & evidence

ORD record
ord-692b7d20e6104fb68f221043b2f49594
Source dataset
uspto-grants-1993_06
Patent number
US05216023

Reaction notes

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