Carbamoylation of amines, thiophenols, mercaptanes and phenols employing organic azides
AssigneeMetkinen Chemistry Oy
InventorsAndrey Yagodkin, Alex Azhayev
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Abstract
The present invention relates to carbamoylation of amines, mercaptanes, thiophenols and phenols employing organic azides. More specifically, the invention relates to a method for generating urea derivatives, thiocarbamate derivatives and carbamate derivatives, and is based on the intermediate formation of isocyanate, starting from an organic azide. The reaction as described is useful in applications for modified nucleoside synthesis, oligonucleotide synthesis, as well as modification, labeling and conjugation of polymers and biomolecules.
Claims13
A method for the preparation of a compound of formula IV
- R—NH—CO—X—R′ (IV)
- wherein
- —R is an aliphatic or aromatic organic group, and
- R′ is an aliphatic organic group and X is NH;
- S or NR″, wherein R″ is alkyl;
- or
- R′ is an aromatic organic group and X is S or O,
- comprising
- (a) reacting a compound of formula R—N3 (II), wherein R is as defined above, with a compound of trivalent phosphorous in the presence of an aqueous solution of hydrogen carbonate ions, in an organic solvent, to obtain an isocyanate of formula III
- —R—N═C═O— (III)
- wherein R is as defined above, and
- (b) reacting the isocyanate of formula III with a compound of formula R′—XH, wherein R′ and X are as defined above,
- to obtain a compound of formula IV.
The method according to 1, wherein the organic solvent is selected from the group consisting of 1,4-dioxane, tetrahydrofurane and acetonitrile.
Dependencies are inferred from the claim text.