ChemicalBook CAS DataBase List Bimatoprost

Bimatoprost synthesis

10synthesis methods

Product Name:Bimatoprost
CAS Number:155206-00-1
Molecular formula:C25H37NO4
Molecular Weight:415.57

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155206-00-1
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Yield:155206-00-1 91%

Reaction Conditions:

Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamidewith hydrogenchloride;water in tetrahydrofuran at 20; for 18 h;
Stage #2: in tetrahydrofuran; pH=6.8;Aqueous phosphate buffer;

Steps:

3

Preparation of the compound X (Bimatoprost)HCl 1.2 N (2 mL) is added at room temperature to a solution of the compound IX (950 mg, 1.5 mmoles) in a tetrahydrofuran/water 1:1 (50 mL) mixture, the reaction is performed under vigorous stirring and is complete after approximately 18 hours. It is quenched by adding phosphate buffer (pH = 6.8, 150 mL), then the organic phase is diluted with AcOEt, the two phases are separated, the aqueous phase is extracted with AcOEt, the re-combined organic phases are dried on magnesium sulphate and filtered, and lastly the solvent is removed at reduced pressure. The product is purified by means of column chromatography (AcOEt-methanol 95:5 v/v) . The Bimatoprost is obtained pure as a colourless oil with a yield of 91%.

References:

WO2010/97672,2010,A1 Location in patent:Page/Page column 20