L-Lysine → HCID 178462329, compound

HRID 1766635Notes

Reaction equation

HRID 1766635 reaction equation
Br[C@:2]1([C@H:10]([CH3:12])[OH:11])[O:7][C:5](=[O:6])[C:4]([OH:8])=[C:3]1[O-:9].[NH2:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19]>N1C=CC=CC=1>[NH2:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[O:6]=[C:5]1[O:7][C@H:2]([C@H:10]([CH3:12])[OH:11])[C:3]([O-:9])=[C:4]1[OH:8]

Participants

4

Reactant 2

HCID 5962L-LysineHCID 178462218HCID 178462218, compound

Product 1

HCID 178462329HCID 178462329, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

6-Deoxybromo ascorbate (8 mmoles) is reacted with lysine (10 mmoles) in dry pyridine to give the desired product. The α-amino group of lysine is protected so that the ε-group is available for reaction. The reaction is carried out overnight. Pyridine is removed under reduce pressure, poured in ice, extracted with ether, washed with water, dried over sodium sulfate. Ether is removed and crystallized from ethanol.

Sources & evidence

ORD record
ord-8ba422fb9f804b9f993b39bebd21d3b1
Source dataset
uspto-grants-2007_06
Patent number
US07230124B2

Reaction notes

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