Process for the preparation of ε-alkoxycarbonyllysines and their analogues
AssigneeF.I.S. Fabbrica Italiana Sintetici S.p.A.
InventorsSiro Serafini, Riccardo Motterle, Elena Brasola
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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.
Claims28
Process for the preparation of an ω-alkoxycarbonylamino-α-aminoacid of formula 1
- wherein n is a number from 2 to 6,
- R1 is C1-C12 alkyl, C1-C12 cycloalkyl or C1-C6 alkenyl, all optionally substituted with aryl, heteroaryl, halogen, C1-C4 alkylthio, C1-C4 alkylsulphonyl, arylsulphonyl, or trimethylsilyl, wherein aryl and heteroaryl may be substituted or unsubstituted,
- R2 is hydrogen or methyl, optionally substituted with halogen atoms,
- comprising reacting in a solvent an α,ω-diaminoacid of formula 2
- wherein n and R2 have the same meaning as above,
- with a 1-alkoxycarbonylbenzotriazole of formula 3
- wherein R1 has the same meaning as above and R3 means from 0 to 2 substituents chosen from the group consisting of methyl, trifluoromethyl, chlorine, bromine and nitro.
A complex of formula (7)
- wherein n is a number from 2 to 6, R1 is t-butyl, R2 is hydrogen or methyl, optionally substituted with halogen atoms, and R3 means from 0 to 2 substituents chosen from the group consisting of methyl, trifluoromethyl, chlorine, bromine and nitro.
Dependencies are inferred from the claim text.