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US 2019/0047933 A1Published application
Process for the synthesis of (2e, 4e, 6z, 8e)-8-(3,4-dihydronaphthalen-1(2h)-ylidene)-3,7-dimethylocta-2, 4, 6-trienoic acid
AssigneeBrickell Biotech, Inc.
InventorsUlrich Abel, József Répási, András Szabó, Cserépi Stefánia Szücsné, Ádám Bor
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Abstract
This invention relates to a novel method for the synthesis of (2E,4E,6Z,8E)-8-(3,4-dihydronaphthalen-1(2H)-ylidene)-3,7-dimethylocta-2,4,6-trienoic acid. In particular, the invention relates to several improvements in several individual steps of the multi-step synthesis scheme
Claims14
A method for the synthesis of MRZ-20321 comprising one or more of the steps of:
- (a) synthesizing E-2/Z-2 by performing a bromination of 1 in a solvent selected from benzotrifluoride and 1,3-bis(trifluoromethyl)benzene, particularly benzotrifluoride;
- (b) lithiating 1;
- (c) adding tetralone to lithiated 1;
- (d) synthesizing Z-7 starting from Z-5, wherein said method comprises the step of synthesizing the methyl ester Z-6;
- (e) reducing Z-6 to obtain Z-7;
- (f) oxidizing Z-7 with stabilized 2-iodoxybenzoic acid (SIBX);
- (g) reacting Z-8 with E-3/Z-3 in the presence of a lithium dialkylamide, particularly lithium diisopropylamide or lithium diethylamide, particularly lithium diisopropylamide;
- and/or
- (h) recrystallizing MRZ-20321 from isopropanol or from n-heptane or from mixtures of n-heptane and 2-methyl tetrahydrofuran.
6 more elements
Dependencies are inferred from the claim text.