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US 2010/0168460 A1Published application
Process for the preparation of (2r,3s)-3-phenylisoserine methyl ester acetate salt
AssigneeIndena S.p.A.
InventorsDaniele Ciceri, Bruno Gabetta, Nicola Vignola, Frieder Mitzel, Beat T. Weber
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Abstract
A process for the enantioselective preparation of (2R,3S)-3-phenylisoserine methyl ester acetate salt of formula (I) which is an useful building block for the synthesis of taxane derivatives. The process involves the resolution of racemic threo-phenylisoserine amide and its conversion into (I).
Claims6
A process for the preparation of (2R,3S)-3-phenylisoserine methyl ester acetate salt (I)
- which comprises the following steps:
- a) treatment of racemic threo 3-phenylisoserine amide (VI)
- with an enantiomerically pure organic acid to provide a corresponding acid salt of (2R,3S)-3-phenylisoserine amide;
- b) treatment of the acid salt of (2R,3S)-3-phenylisoserine amide with a strong inorganic acid in a protic solvent to provide a (2R,3S)-3-phenylisoserine amide inorganic acid salt;
- c) treatment of the (2R,3S)-3-phenylisoserine amide inorganic acid salt with hydrochloric acid in a protic solvent followed by treatment with acetic acid to crystallise (2R,3S)-3-phenylisoserine methyl ester acetate salt (I).
2 more elements
(2R,3S)-3-Phenylisoserine amide in the form of a salt with (−)-tartaric or (−)-dibenzoyltartaric acid.
(2R,3S)-3-Phenylisoserine amide hydrochloride.
Dependencies are inferred from the claim text.