L-Lysine → HCID 178462329, compound

HRID 983507Notes

Reaction equation

HRID 983507 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-814978a83f8a49ae8205ed4ab02064cc
Source dataset
uspto-grants-2005_03
Patent number
US06864284B2

Reaction notes

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