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Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, ethyl ester synthesis

6synthesis methods
153559-49-0 Synthesis
Bexarotene

153559-49-0
276 suppliers
$28.00/5mg

Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-, ethyl ester

1346970-00-0
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Yield:-

Reaction Conditions:

with dmap;N-(3-dimethylaminopropyl)-N-ethylcarbodiimide in dichloromethane;N,N-dimethyl-formamide at 20;

Steps:

2.2.1. General synthetic scheme for esterification

General procedure: Ester prodrugs of BEX and RA were synthesised by adding2.87 mmol of the desired alcohol to 0.287 mmol of BEX or RA. 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (0.431 mmol) and 4-dimethylaminopyridine(0.057 mmol) were added, and dichloromethane(15 mL) was used as the solvent. The mixture was stirred magneticallyovernight at room temperature. Purification was performed by flashchromatography using a 200-400 mesh silica gel-packed glass columnsand hexane-ethyl acetate 50:2 (v/v) as the mobile phase. Specific detailsfor compounds that were obtained by different synthetic schemesare described in Supplementary Material 1

References:

Lee, Jong Bong;Zgair, Atheer;Malec, Jed;Kim, Tae Hwan;Kim, Min Gi;Ali, Joseph;Qin, Chaolong;Feng, Wanshan;Chiang, Manting;Gao, Xizhe;Voronin, Gregory;Garces, Aimie E.;Lau, Chun Long;Chan, Ting-Hoi;Hume, Amy;McIntosh, Tecashanell M.;Soukarieh, Fadi;Al-Hayali, Mohammed;Cipolla, Elena;Collins, Hilary M.;Heery, David M.;Shin, Beom Soo;Yoo, Sun Dong;Kagan, Leonid;Stocks, Michael J.;Bradshaw, Tracey D.;Fischer, Peter M.;Gershkovich, Pavel [Journal of Controlled Release,2018,vol. 286,p. 10 - 19]