L-Lysine → HCID 86615832, compound

HRID 1816854Notes

Reaction equation

HRID 1816854 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:18])OC(=O)[CH2:14][CH2:13][CH2:12]1.C[N:20]([CH:22]=[O:23])C>CN(C)C1C=CN=CC=1>[C:11]([NH2:1])(=[O:18])[CH2:12][CH2:13][CH2:14][C:22]([NH2:20])=[O:23].[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 6228DimethylformamideHCID 7940Glutaric anhydride

Product 1

HCID 86615832HCID 86615832, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

In this example that demonstrates how this method could be performed, 5 g Lysine, 8.7 g glutaric anhydride and 2.0 g 4-Dimethylaminopyridine (DMAP) are weighed into a 100 ml flask fitted with a condenser and nitrogen inlet. 100 ml DMF is added and the mixture stirred under nitrogen atmosphere for 5 min and immersed into an oil bath preheated to 90° C. for 1.5 h until HPLC assay indicated completion of reaction. DMF is evaporated under vacuum (distilled below 40° C. and the residue is used directly for the subsequent reaction. The residue can be purified by chromatography on silica gel.

Workup

  1. customfitted with a condenser and nitrogen inlet
  2. customimmersed into an oil bath
  3. waitpreheated to 90° C. for 1.5 h until HPLC assay
  4. customcompletion of reaction
  5. customDMF is evaporated under vacuum (
  6. distillationdistilled below 40° C.
  7. customthe residue is used directly for the subsequent reaction
  8. customThe residue can be purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cb3eda1f623b4d299c253947c39dfc07
Source dataset
uspto-grants-2009_10
Patent number
US07597882B2

Reaction notes

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