- Aspirination of α-aminoalcohol (sarpogrelate M1)
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Aspirination of α-aminoalcohol (sarpogrelate M1) has been performed under various general esterification conditions. In most cases, the desired aspirinate ester was obtained at a low yield with unexpected byproducts, the formation of which was mostly derived from the chemical properties of the tertiary α-amino group. After systematic analysis of those methods, the aspirinated sarpogrelate M1 was prepared using a two-step approach combining salicylate ester formation and acetylation.
- Park, Sunhwa,Lee, Jiyun,Shin, Kye Jung,Seo, Jae Hong
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- Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate
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(Chemical Equation Presented) Triethylamine (Et3N) mediates esterification reactions between the title reagent (1) and carboxylic acids. Alcohols, phenols, amides, and other sensitive functionality are not affected; a dual role for Et3N as a promoter and a scavenger is postulated. Benzyl esters are obtained from substrates including amino acid and sugar derivatives.
- Tummatorn, Jumreang,Albiniak, Philip A.,Dudley, Gregory B.
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p. 8962 - 8964
(2008/03/12)
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- Aspirin prodrugs: synthesis and hydrolysis of 2-benzyloxy-2-methyl-4H-1,3-benzodioxin-4-ones.
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Aspirin is widely used for its analgesic, antiinflammatory and antipyretic properties. Among its disadvantages are the relatively narrow therapeutic margin, its irritancy towards the gastric mucosa, and occasionally patient hypersensitivity towards aspirin. As part of our effort to develop prodrugs without these liabilities eleven new title compounds have been isolated and characterized. These 'superaspirin' candidates were subjected to non-enzymatic hydrolysis for a first rapid screening in vitro. Only 2-(2,6-dimethoxybenzyloxy)-2-methyl-4H-1,3-benzodioxin-4-one (4c) was observed to act as an exclusive aspirin prodrug, while 2-(2-methoxybenzyloxy)-2-methyl-4H-1,3-benzodioxin-4-one (4b) and 2-(2-ethoxybenzyloxy)-2-methyl-4H-1,3- benzodioxin-4-one (4d) were shown to release both aspirin 6 and salicylic acid 7. Subsequently, these three candidates were further characterized by investigation of the pH profile of their hydrolysis rates.
- Ankersen,Senning
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p. 793 - 798
(2007/10/02)
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