METHOD OF OBTAINING CHIRAL S-MONOTHERPENALCISTINES Russian patent published in 2018 - IPC C07C319/14 C07C323/58 C07C323/61 

FIELD: technological processes.

SUBSTANCE: proposed method for producing chiral S-monoterpenyl cysteines involves reaction of nucleophilic substitution and is characterized in that synthesis of compounds is carried out in one stage by introducing compact lipophilic fragment of monoterpenes into structure of a known biologically active L-amino acid. Reaction of nucleophilic substitution of the chlorine atom in L-3-chloroalanine for monoterpenyl thiolate ion generated in sodium hydride-DMF system, is carried out at temperature from 0 to 25 °C when the ratio of thiol:L-3-chloroalanine:NaH=1:1:1.5, respectively. 4-quarantiol, 3-hydroxyisocarathiol, neomentanethiol, 10-thioisoborneol, 10-hydroxyisocamphenylthiol or 10-thioisocampheol are used as starting terpene thiols, thus obtaining terpene derivatives of the general formula given below. Asterisks indicate bond through which reaction of addition to sulfanyl group is carried out.

R₁ - ; R₂ - ;

R₃ - ; R₄ - ;

R₅ - ; R₆ - .

EFFECT: invention may find application in organic synthesis for the production of biologically active substances and in the pharmaceutical industry as intermediates in the synthesis of drugs.

1 cl, 6 ex