METHOD OF PRODUCING MONOPROTECTED α,ω-DIAMINOALCANES Russian patent published in 2021 - IPC C07C269/06 C07C271/12 C07C271/20 C07C271/22 

FIELD: organic chemistry.

SUBSTANCE: invention relates to a method for the synthesis of monoprotected, α,ω-diaminoalkanes, and in particular to a method for the synthesis of a compound of Formula(III). The method includes steps a) and b). In step a), the compound of Formula (I) is converted to the compound of Formula (II) by reacting the compound of Formula (I) with the compound of Formula (IV) in the presence of a binding reagent. In step b), the compound of Formula (II) is treated with a borane reagent, followed by acid hydrolysis to obtain the compound of Formula (III). In the above formulas R and R¹ are independently selected from H, (CH₂)_nOCH₃, (CH₂CH₂O)_nH, (CH₂CH₂O)_nCH₃, (CH₂)_nNHP, (CH₂)_nN(CH₃)₂, (CH₂)_nNHCONH₂, (CH₂)_nNHSO₂CH₃, (CH₂)_nSO₂NH₂, C_1-8 alkyl, potentially substituted, C_3-15 cycloalkyl, potentially substituted, and C_3-15 heterocycloalkyl, potentially substituted, P is a protective group, m stands for a whole number from 1 to 3 and n stands for a whole number from 1 to 12. The invention also relates to the use of this method in the process of synthesis of a drug compound-a linker containing α,ω-diaminoalkane fragment, as well as in the process of obtaining antibody-drug conjugates.

EFFECT: proposed method is effective and makes it possible to obtain a compound of Formula (III) with a good yield and chemical purity.

15 cl, 2 ex