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2 538 604

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IPC

C07C57/03(2006-01-01)

C07C51/31(2006-01-01)

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Application

2013136788/04, 2013-08-06

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Start date

2013-08-06

(22)

Actual filing date

2013-08-06

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Published

2015-01-10

(72)

Inventor

Dzhemilev Usein MemetovichD'Jakonov Vladimir Anatol'EvichMakarov Aleksej AleksandrovichDzhemileva Lilja UseinovnaMakarova Ehlina KhamzinovnaKhusnutdinova Ehl'Za Kamilevna

(73)

Holder

Federal'Noe Gosudarstvennoe Bjudzhetnoe Uchrezhdenie Nauki Institut Neftekhimii I Kataliza Rossijskoj Akademii NaukFederal'Noe Gosudarstvennoe Bjudzhetnoe Uchrezhdenie Nauki Institut Biokhimii I Genetiki Ufimskogo Nauchnogo Tsentra Rossijskoj Akademii Nauk

METHOD OF OBTAINING (5Z,9Z)-5,9-HEXADECADIENOIC ACID Russian patent published in 2015 - IPC C07C57/03 C07C51/31

Abstract RU 2538604 C1

FIELD: chemistry.

SUBSTANCE: invention relates to field of obtaining (5Z,9Z)-5,9-hexadecadienoic acid of formula , demonstrating inhibiting action on human topoisomerase I. (5Z,9Z)-5,9-hexadecadienoic acid is promising as medication, possessing anti-tumour, antiviral and antibacterial action. Essence of method consists in interaction of tetrahydropyrane ether of 5,6-heptadien-1-ol (5) and 1,2-nonadiene (6) with Grignard reagent RMgX (R = Me, Et, Pr, Bu, Oct; X = Cl, Br, I) in diethyl ether in presence of metallic Mg (powder) and catalyst titanocene dichloride Cp₂TiCl_2,with molar ratio (5):(6): RMgX : Mg : Cp₂TiCl₂= 10:12:30-50:32:0.4-0.6), in argon atmosphere at temperature 0-35°C and atmospheric pressure for 6-10 h. After that, reaction mass is processed with 5% water HCl solution with obtaining 2-[(5Z,9Z)-5,9-hexadecadien-1-yloxy]tetrahydro-2H-pyrane (7), which is oxidized with Jones reagent.

EFFECT: method makes it possible to obtain individual formula compound in two preparative stages with high output.

15 ex, 1 tbl

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RU 2 538 604 C1

Authors

Dzhemilev Usein Memetovich

D'Jakonov Vladimir Anatol'Evich

Makarov Aleksej Aleksandrovich

Dzhemileva Lilja Useinovna

Makarova Ehlina Khamzinovna

Khusnutdinova Ehl'Za Kamilevna

Dates

2015-01-10—Published

2013-08-06—Filed