L-Lysine → HCID 67512501, compound

HRID 1816853Notes

Reaction equation

HRID 1816853 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]1(=[O:17])O[C:14](=[O:15])[CH2:13][CH2:12]1.C(N(CC)CC)C>CN(C)C=O>[C:11]1(=[O:17])[NH:1][C:14](=[O:15])[CH2:13][CH2:12]1.[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 3

HCID 5962L-LysineHCID 7922Succinic anhydrideHCID 8471Triethylamine

Product 1

HCID 67512501HCID 67512501, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In this example that demonstrates how this method could be performed, 2 g of L-lysine is dissolved in 200 ml dry N,N-dimethyl formamide (DMF) in a 500 ml round bottom flask. 10.7 g succinic anhydride and 20 ml triethyl amine are added under nitrogen atmosphere. The mixture is heated to 60° C. for 6 h. At the end of 6 h period, the solution is cooled and solvent is removed by vacuum distillation. The crude product is purified by flash chromatography. It is then immediately used in next reaction.

Workup

  1. temperatureAt the end of 6 h period, the solution is cooled
  2. customsolvent is removed by vacuum distillation
  3. customThe crude product is purified by flash chromatography
  4. customIt is then immediately used in next reaction

Sources & evidence

ORD record
ord-57dc5b50b9864293a1edba7736cc6c75
Source dataset
uspto-grants-2009_10
Patent number
US07597882B2

Reaction notes

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