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

Participants

Role	Name	HCID	Charge
Reactant	L-Lysine monohydrochloride	HCID 69568	—
Reactant	Carbonic acid, 1,1-dimethylethyl phenyl ester	HCID 81113	—
Reactant	HCID 178418385	HCID 178418385	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acid	HCID 2733283	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08026372B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-879078d31af743c9814b9a010209293f
Source note	uspto-grants-2011_09