Process for the recovery of beta acetylfuranoside

Patent metadata

Field	Value
Publication number	US-9580455-B2
Application number	US-201213675220-A
Country	US
Kind code	B2
Filing date	Nov 13, 2012
Priority date	Jan 27, 2009
Publication date	Feb 28, 2017
Grant date	Feb 28, 2017

Abstract

There is provided an improved method for the recovery of residual, unseparated β-acetylfuranoside from reaction mixtures remaining from an initial synthesis of acetylfuranoside, 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-acetylfuranoside from mother liquor remaining from the synthesis of acetylfuranoside (ACF), 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; 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.

2. The process according to claim 1 , 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

• C07H1/00 Primary

  Processes for the preparation of sugar derivatives · CPC title

• C07H1/06

  Separation; Purification · CPC title