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US 11,912,654 B2Granted
Process for stereospecific synthesis of vitamin K2 and its novel intermediates
AssigneeSynergia Life Sciences Pvt. Ltd.
InventorsDilip Mehta, Mayank Shashtri, BNS Raju, Ashwin Shah, Parin Vora, Umakant Mahale
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Abstract
The present disclosure relates to a novel process for the synthesis of stereospecific compounds of Vitamin K2 group in general and Vitamin K2-7. The present disclosure further discloses novel intermediates useful in the synthesis of stereospecific Vitamin K2-7. Compounds of the Vitamin K2 group obtained are crystalline and exhibit well defined melting points.
Claims3
A process for the synthesis of Vitamin K2 of Formula I,
- wherein n is 3 or 4, and the process comprises:
- (a) adding menadione/cyclopentadiene adduct to t-butanol:toluene mixture that is in the range of 10:90 to 20:80 v/v, at a temperature ranging from 20° C. to 40° C.;
- (b) dissolving potassium t-butoxide in reaction mixture of (a);
- (c) adding prenyl chloride to the reaction mixture of (b) and stirring the mixture for an hour;
- (d) quenching the reaction mixture of (c) in distilled water;
- (e) adjusting the pH of the reaction mixture of (d) to 5-6 and isolating the non-aqueous layer;
- (f) washing the non-aqueous layer of (e) with water and brine, and drying the washed non-aqueous layer over sodium sulfate;
- (g) recovering the product Vitamin K2-3 from the non-aqueous layer of (f) by reflux and distilling off the solvent under vacuum, wherein Vitamin K2-3 has the chemical structure:
- (h) converting the Vitamin K2-3 obtained in (g) into its dibenzyl ether having the chemical structure:
- wherein Ph is a phenyl group;
- (i) converting the dibenzyl ether of Vitamin K2-3 obtained in (h) into its bromohydrin derivative in the presence of N-bromo succinamide and tetrahydrofuran, wherein the bromohydrin derivative of dibenzyl ether of vitamin K2-3 has the chemical structure:
- (j) converting the bromohydrin derivative of dibenzyl ether of vitamin K2-3 obtain in (i) to its epoxide in the presence of potassium carbonate and methanol, wherein the epoxide derivative of dibenzyl ether of vitamin K2-3 has the chemical structure:
- (k) converting the epoxide derivative of dibenzyl ether of vitamin K2-3 obtained in (j) into Vitamin K2-3 alcohol in the presence of aluminium isopropoxide in toluene, wherein the Vitamin K2-3 alcohol has the chemical structure:
- (l) reacting the Vitamin K2-3 alcohol obtained in (k) with thionyl chloride in hexane to form Vitamin K2-3 chloride having the chemical structure:
- (m) reacting the Vitamin K2-3 chloride obtained in (l) with a prenyl phenyl sulphonate to obtain a compound, wherein the prenyl phenyl sulphonate is selected from:
- (n) desulphonating, deprotecting, and oxidizing the compound obtained in (m) to obtain Vitamin K2 of Formula I.
13 more elements
Dependencies are inferred from the claim text.