L-Lysine monohydrochloride → (2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acid

HRID 913377

Reaction equation

HRID 913377 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].N1C2C=CC=CC=2N=N1.[C:21](=O)([O:27]C1C=CC=CC=1)[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>O.C1COCC1>[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:21]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:27]

Participants

6

Reactant 3

HCID 69568L-Lysine monohydrochlorideHCID 81113Carbonic acid, 1,1-dimethylethyl phenyl esterHCID 178418385HCID 178418385, compound

Product 1

HCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of L-lysine monohydrochloride (20.0 g, 109.5 mmol) and benzotriazole (14.3 g, 120.0 mmol) in a mixture of water (66.6 mL) and THF (111.0 mL) at pH 12 was treated with t-butyl phenyl carbonate (24.3 mL, 131.4 mmol) and stirred 18 hours at 60° C. The mixture, initially 2 layers, became a clear orange solution and the product was approximately 75% (NMR).

Sources & evidence

ORD record
ord-879078d31af743c9814b9a010209293f
Source dataset
uspto-grants-2011_09
Patent number
US08026372B2

Linked notes

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