Methods of preparing N6-((2-azidoethoxy)carbonyl)lysine
AssigneeSanofi
InventorsHans Aerni, Randall Scheuerman, Nikolai F. Sepetov, Alexander V. Shirokov
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Abstract
Disclosed herein are methods of preparing N6-((2-azidoethoxy)carbonyl)lysine, N6-((2-azidoethoxy)carbonyl)-L-lysine, and N6-((2-azidoethoxy)carbonyl)-D-lysine. Also disclosed herein are the compounds tert-butyl N2-(tert-butoxycarbonyl)-N6-((2-chloroethoxy)carbonyl)-L-lysinate and tert-butyl N6-((2-azidoethoxy)carbonyl)-N2-(tert-butoxycarbonyl)-L-lysinate, and uses thereof.
Claims30
A method of preparing a compound of Formula (VI)
- or a salt thereof,
- comprising reacting a compound of Formula (III)
- with an acid to afford the compound of Formula (VI) or a salt thereof.
A method of preparing a compound of Formula (III)
- comprising reacting a compound of Formula (II)
- wherein R1 is selected from chloro, bromo, and iodo,
- with an alkali azide salt to afford the compound of Formula (III).
A method of preparing a compound of Formula (II)
- comprising reacting a compound of Formula (I)
- with a compound of Formula (V)
- to afford the compound of Formula (II),
- wherein in each of the compounds of Formula (I) and Formula (II), R1 is the same and is selected from chloro, bromo, and iodo.
A method of preparing a compound of Formula (I)
- comprising reacting a compound of Formula (IV)
- with N-hydroxysuccinimide to afford the compound of Formula (I),
- wherein in each of the compounds of Formula (I) and Formula (IV), R1 is the same and is selected from chloro, bromo, and iodo.
A method of preparing a compound of Formula (VIa), or a salt thereof, comprising the following steps:
- (i) reacting
- with
- to form
- (ii) reacting
- with
- to form
- (iii) reacting
- with NaN3 to form
- and
- (iv) reacting
- with HCl to form
- or a salt thereof.
A compound selected from:
- a) a compound of Formula (I):
- wherein R1 is selected from chloro, bromo, and iodo;
- b) a compound of Formula (II):
- wherein R1 is selected from chloro, bromo, and iodo;
- c) a compound of Formula (III):
- d) a compound of Formula (VII):
- wherein:
- R3 is selected from chloro, bromo and iodo;
- R4 is selected from —OR6, —CF3, —CH2C6-C12aryl, and C1-C6 alkyl;
- R5 is —CH2C6-C12aryl or C1-C6 alkyl;
- and
- R6 is selected from C1-C6 alkyl, C6-C12aryl, and —CH2C6-C12 aryl;
- and
- e) a compound of Formula (VIII):
- wherein:
- R7 is selected from —OR9, —CF3, —CH2C6-C12aryl, and C1-C6 alkyl;
- R8 is —CH2C6-C12aryl or C1-C6 alkyl;
- and
- R9 is selected from C1-C6 alkyl, C6-C12aryl, and —CH2C6-C12aryl.
Dependencies are inferred from the claim text.