Process for the preparation of 3,4-dihydroxybutanoic acid...

C - Chemistry – Metallurgy – 07 – C

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C07C 51/285 (2006.01) C07C 59/10 (2006.01) C07D 307/33 (2006.01)

Patent

CA 2360864

A process for the preparation of 3,4-dihydroxybutanoic acid (I) and 3-hydroxy- .gamma.-butyrolactone (V) thereof from a 3-leaving group substituted pentose source is described. In particular, the process relates to the synthesis of (R)-3,4-dihydroxybutanoic acid and (R)-3-hydroxy-.gamma.-butyrolactone from a 3-leaving group substituted L- pentose sugars. The process uses a base and a peroxide to convert the pentose source to the chiral 3,4-dihydroxybutanoic acid compound. The chiral 3,4-dihydroxybutanoic acid can be further converted to 3-hydroxy-.gamma.-butyrolactone by acidification. The chiral compound is useful as a chemical intermediate to the synthesis of various drugs and other products.

L'invention concerne un procédé de préparation d'acide 3,4-dihydroxybutanoïque (I) et de 3-hydroxy- gamma -butyrolactone (V) correspondant à partir d'une source de pentose substituée par un groupe 3 labile. Notamment, le procédé concerne la synthèse de l'acide (R)-3,4-dihydroxybutanoïque et de (R)-3-hydroxy- gamma -butyrolactone à partir d'une source de L-pentose substituée par un groupe 3 labile. Le procédé met en oeuvre une base et un peroxyde pour convertir la source de pentose en un composé d'acide 3,4-dihydroxybutanoïque chiral. L'acide 3,4-dihydroxybutanoïque chiral peut être encore converti en 3-hydroxy- gamma -butyrolactone par acidification. Le composé chiral est utile en tant qu'intermédiaire chimique à la synthèse de divers médicaments et d'autres produits.

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