Novel Process for the Recovery of Beta Acetylfuranoside

Patent metadata

Field	Value
Publication number	US-2016333040-A9
Application number	US-201213675220-A
Country	US
Kind code	A9
Filing date	Nov 13, 2012
Priority date	Jan 27, 2009
Publication date	Nov 17, 2016
Grant date	—

Abstract

There is provided an improved method for the recovery of residual, unseparated β-ACF from reaction mixtures remaining from an initial synthesis of ACF, which is in particular usable on a large industrial scale, more particularly in the production of capecitabine.

First claim

What is claimed:

1 . A method for recovery of initially not separated β-ACF from mother liquor remaining from the synthesis of ACF, wherein the β-ACF is recovered by a combination of at least one distillation method and at least one chemical reaction step.

2 . The method according to claim 1 comprising the following sequential steps:
a) Evaporation to less than 1% residual solvent of the mother liquor remaining from an initial synthesis of ACF, to increase the content of residual α/β-ACF from about 8 to 15 weight-% to about 25 to 45 weight-%, followed by distillation to about 60 to 80 weight-% and subsequent crystallization of β-ACF out of the distillate by adding a suitable solvent;
b) Chemical conversion of α/β-ACF mixture remaining in the mother liquor of step a), to β-ACF by de-acetylation and subsequent re-acetylation, followed by crystallization of β-ACF by addition of a suitable solvent;
c) Optional repetition of step a) and b) in a sequential (clockwise) cyclic process.

3 . The process according to claim 2 , wherein the distillation to about 60 to 80 weight-% of step a) is carried out at 1 to 3 mbar and 200 to 210° C. heating temperature in a continuous thin-film evaporator.

4 . The process according to claim 3 , wherein step b) comprises the de-acetylation of α/β-ACF in the presence of a suitable base, followed by neutralization with a suitable acid and further followed by the re-acetylation reaction in the presence of suitable base, a suitable catalyst and a suitable acetylating agent.

Assignees

• Hoffmann La Roche

Inventors

• Behringer Martin
• Junghans Bernd
• Knipp Bernhard
• Pfeil Bernhard
• Zieres Gerald

Classifications

• C07H13/04 Primary

  having the esterifying carboxyl radicals attached to acyclic carbon atoms · CPC title

• C07H1/06

  Separation; Purification · CPC title

• C07H1/00 Primary

  Processes for the preparation of sugar derivatives · CPC title