Bempedoic acid synthesis
- Product Name:Bempedoic acid
- CAS Number:738606-46-7
- Molecular formula:C19H36O5
- Molecular Weight:344.49
ETC-1002 (Bempedoic acid, ESP-55016) is an orally available, LDL-C lowering small molecule that is an activator of hepatic AMPK. It is synthesized by the hydrolysis of 8-keto-2,2,14,14-tetramethylpentadecanedioic acid in purified water and sodium hydroxide.
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Yield:738606-46-7 97.9%
Reaction Conditions:
Stage #1:8-oxo-2,2,14,14-tetramethylpentadecanedioic acid with sodium hydroxide in water at 20; for 0.5 h;
Stage #2: with sodium tetrahydroborate;water for 4 h;Reagent/catalyst;Temperature;
Steps:
1 Exmaple 1:
5.0 g (14.6 mmol) of 8-keto-2,2,14,14-tetramethylpentadecanedioic acid was poured into 50 ml of purified water.1.46 g (36.5 mmol) of sodium hydroxide was added, and the mixture was continuously stirred until completely dissolved. After reacting at 20 ° C for 30 minutes,0.55 g (14.6 mmol) of sodium borohydride was added to the reaction solution, and the reaction was continued for 4 hours.The TLC dot plate (developing agent ethyl acetate: n-hexane: acetic acid = 1:5:0.3) was completely reacted.Concentrated hydrochloric acid was added to the reaction solution, and the pH was adjusted to 1, and after stirring for 10 minutes, methyl t-butyl ether was added to 60 ml × 3 times to extract the organic layer.The solution was washed with 60 ml of purified water, and the organic layer was separated, washed twice with saturated brine (60 ml), dried over anhydrous sodium sulfateThe white solid was obtained as 8-hydroxy-2,2,14,14-tetramethylpentadecanedioic acid in a yield of 97.9% and a purity of 99.3%.
References:
Lunan Pharmaceutical Group Co., Ltd.;Zhang Guimin;Duan Liangxing;Wang Jun CN109721486, 2019, A Location in patent:Paragraph 0025-0047