L-Lysine → HCID 86759189, compound

HRID 986872Notes

Reaction equation

HRID 986872 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[OH-:11].[Na+].C(=O)(O)[O-].[Na+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>O.C(O)C>[N+:25]([C:22]1[CH:23]=[CH:24][C:19]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:26])=[O:11])=[CH:21][CH:20]=2)=[CH:20][CH:21]=1)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 5962L-LysineHCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 86759189HCID 86759189, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5 g (34.2 mmol) of L-lysine are dissolved in 100 ml of water in the presence of 1.4 g (1 eq) of sodium hydroxide and 8.6 g (3 eq) of sodium bicarbonate in a 250 ml three-necked flask equipped with a reflux condenser and a thermometer. A solution of 10.8 ml (3 eq) of 4-fluoronitrobenzene in 60 ml of ethanol is run into the mixture, which is brought to reflux (85°-90° C.) for 5 days. The cooled mixture is extracted with ethyl ether. The aqueous phase is acidified to pH˜3 with 5N hydrochloric acid. A gummy precipitate is formed, which precipitate is extracted with dichloromethane in the presence of a small amount of methanol. The organic phase is washed with water to neutrality, dried over sodium sulphate and then evaporated to give an orange-colored oil which crystallizes in the presence of ethyl ether. 11.7 g of a yellow crystalline product are obtained, i.e. a yield of 88%.

Workup

  1. customequipped with a reflux condenser
  2. temperatureto reflux (85°-90° C.) for 5 days
  3. extractionThe cooled mixture is extracted with ethyl ether
  4. customA gummy precipitate is formed
  5. customwhich precipitate
  6. extractionis extracted with dichloromethane in the presence of a small amount of methanol
  7. washThe organic phase is washed with water to neutrality
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customto give an orange-colored oil which
  11. customcrystallizes in the presence of ethyl ether

Sources & evidence

ORD record
ord-9452c954460d4ce18001ecd6dbdc93dc
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

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