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ChemicalBook CAS DataBase List EPROSARTAN
133040-01-4

EPROSARTAN synthesis

9synthesis methods
-

Yield:133040-01-4 70.92%

Reaction Conditions:

Stage #1:2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde;3-ethoxy-3-oxo-2-(thien-3-ylmethyl)propanoic acid with piperidine;hydrogenchloride in di-isopropyl ether;water at 40 - 55; under 760.051 Torr;Heating / reflux;
Stage #2: with water;sodium hydroxide in methanol for 3 h;Heating / reflux;
Stage #3: with hydrogenchloride in methanol;water; pH=5.0 - 5.2 at 35 - 40;

Steps:

3
Example 3: Preparation of Eprosartan.11 To diisopropyl ether (125 ml) was added piperidine (4.7 g, 0.0551 mol) and hydrochloric acid (2.5ml) at 25-300C. The contents were heated to 40-450C, followed by addition of the compound (25 g,0.0833 mol) as prepared in Example 2 above. The reaction mass was heated to a temperature of 50-55°C and Ethyl 2-carboxy-3-(2-thienyl) propionate (43 g, 0.189 mol) added in 3 lots. The contents were heated to reflux under reduced pressure in a Dean-Stark apparatus until reaction completion. Thereafter the excess solvent was completely removed under vacuum, methanol was added to the crude residue, followed by sodium hydroxide solution. The contents were heated to reflux for 3 hours, cooled to 35-4O0C, pH adjusted to 5.0- 5.2 using 10% HCl. The contents were cooled to 200C with stirring for 2 hours. The product was filtered and then washed with 50% aq. isopropyl alcohol (1X50 ml), and water (2X25 ml), dried for 1 hour to get the desired compound (40 g).The crude eprosartan base(40gm) is taken in 10% sodium hydroxide (125 ml) at 25-300C and stirred for 15 minutes at 35-400C, followed by filtration through fryflow bed, washed with water. The crude product was taken in isopropyl alcohol(62.5 ml),pH adjusted to 5.0-5.2 with 10% HCl at 35-400C, product cooled to 2O0C and stirred for 2 hours, filtered, washed with 50% aqueous isopropyl alcohol (50 ml) and water (2X25 ml) and dried to get the desired compound (Dry wt 25 g, Yield=70.92%).

References:

NEULAND LABORATORIES LTD WO2009/84028, 2009, A2 Location in patent:Page/Page column 7; 11-12

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