Pidotimod synthesis
- Product Name:Pidotimod
- CAS Number:121808-62-6
- Molecular formula:C9H12N2O4S
- Molecular Weight:244.27
First L-cysteine (1) was reacted with formaldehyde to give L-thiazolidine-4-carboxylic acid (2). L-pyroglutamic acid (3) was reacted with pentachlorophenol in solvent N,N-dimethylformamide (DMF) and with the presence of a condensing agent dicyclohexylcarbodiimide (DCC) to give L-pyroglutamic acid pentachlorophenyl ester (4). The compound (2) reacted with compound (4) in solvent DMF and with deacid agent triethylamine to give pidotimod after dehydration condensation.
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Yield:121808-62-6 47.2 g
Reaction Conditions:
with hydrogenchloride in water for 2 h;
Steps:
3.2 (2) Synthesis of Pidotimod
The above-mentioned product L-thiazolidine-4-carboxylic acid was added to 500 ml of absolute ethanol, and 100 g of thionyl chloride was added dropwise thereto, which was produced as a white gas, and the mixture was heated to reflux for 5 hours. Ethanol was distilled off under reduced pressure, concentrated aqueous ammonia was added dropwise, pH was adjusted to 12, extracted twice with isopropyl acetate, and the ester layer was evaporated to dryness.500 ml of THF was added, and 82 g of L-pyroglutamic acid was added in portions, stirred and dissolved, and then cooled to 0 °C. 125 g of DCC in THF was added dropwise, and the mixture was warmed to room temperature overnight, and an insoluble solid cyclohexylurea appeared during the reaction.Filtration, filter cake washing, and evaporation of the filtrate. The temperature was lowered to 5 ° C, and the potassium hydroxide solution was slowly dropped, and the reaction was completed by TLC. The pH was adjusted to 1 with concentrated hydrochloric acid, and the temperature was lowered and a few pimodex seeds were added. After stirring for 2 hours, a large amount of solid was precipitated, and dried by filtration to obtain 47.2 g.
References:
Guangzhou Da Guang Pharmaceutical Co., Ltd.;Long Zili;Huang Weijing;Chen Weihan CN108640912, 2018, A Location in patent:Paragraph 0018; 0021; 0023; 0025; 0027
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