Process for the preparation of ε-alkoxycarbonyllysines and their analogues

US8026372B2 · kind B2 · utility

Assignee

• F.I.S. Fabbrica Italiana Sintetici S.p.A. · IT

Inventors

• Siro Serafini · Vicenza, IT
• Riccardo Motterle · Arcugnano, IT
• Elena Brasola · Selvazzano Dentro, IT

Key dates

• Filing date: Aug 4, 2006
• Grant date: Sep 27, 2011
• Expiry date: Nov 15, 2026

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D249/18
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

A process for the preparation of ω-alkoxycarbonylamino-α-aminoacids and α,ω orthogonally diprotected diaminoacids from α,ω-diaminoacids using 1-alkoxycarbonylbenzotriazoles as protecting agents is disclosed. In an alternative embodiment, carbamoylating agents in the presence of benzotriazoles are used instead of 1-alkoxycarbonylbenzotriazoles. This reaction is preferably applied to the preparation of ε-alkoxycarbonyllysines from lysine. A process for the preparation of t-butoxycarbonylbenzotriazoles and novel complexes of ω-alkoxycarbonylamino-α-aminoacids with benzotriazoles are also disclosed.