ChemicalBook CAS DataBase List Allisartan Isoproxil

Allisartan Isoproxil synthesis

2synthesis methods

Product Name:Allisartan Isoproxil
CAS Number:947331-05-7
Molecular formula:C27H29ClN6O5
Molecular Weight:553.01

Although several synthetic routes have been reported within two patents, the most likely scalable process route is described in the scheme. Commercial 2-butyl-4-chloro-5-(hydroxymethyl)-imidazole (7) was alkylated with Ntriphenylmethyl- 5-(4'-bromomethylbiphenyl-2-yl)tetrazole (8) under basic conditions in warm DMF, providing alcohol 9 in 90% yield. This alcohol was then oxidized to the corresponding carboxylic acid 10 with KMnO4 in 88% yield. Etherification of acid 10 with isopropyl chloromethyl carbonate (11) followed by de-tritylation of the tetrazole group under acidic contidions gave allisartan isoproxil (II) in 69% yield.

2-butyl-4-chloro-1-[(2'-(1-triphenylmethyl-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl]imidazole-5-carboxylic acid 1-[(isopropoxy)carbonyloxy]methyl ester

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Yield: 92.7%

Reaction Conditions:

with acetic acid in ethanol for 10 h;Product distribution / selectivity;Reflux;

Steps:

3
4.10 g of 2-butyl-4-chloro-1-[2'-(1-triphenylmethyl-1H-tetrazol-5-yl) -1,1'-biphenyl-methyl]-imidazole-5-carboxylic acid, 1-[(isopropoxy)-carbonyloxy] methyl ester (4.93mmol, purity: 95.6%, HPLC normalization method) is dissolved in 50 ml of ethanol, then added with 0.85 ml of glacial acetic acid, heated to reflux and reacted for 10 h. After the reaction, stopping heating, the solution is cooled naturally to the room temperature (24°C). A plenty of solid is precipitated, and filtered. The filtrate is concentrated in reduced pressure to dryness, and 2.48 g white solid is obtained in a yield of 92.7%.

References:

Shanghai Allist Pharmaceuticals, Inc. EP2213669, 2010, A1 Location in patent:Page/Page column 7

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References

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