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US 2010/0249395 A1Published application
Methods for preparing capecitabine and beta-anomer-rich trialkyl carbonate compound used therein
AssigneeHanmi Pharm. Co., Ltd.
InventorsJaeheon Lee, Gha-Seung Park, Weon Ki Yang, Jin Hee Kim, Cheol Hyun Park, Yong-Hoon An, Yoon Ju Lee, Young-Kil Chang, Gwan Sun Lee
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Abstract
The present invention relates to a method for preparing capecitabine and a method for preparing a β-anomer-rich trialkyl carbonate compound used therein, and a highly pure capecitabine can be efficiently prepared with a high yield by the method of the present invention using the β-anomer-rich trialkyl carbonate compound as an intermediate.
Claims7
A method for preparing capecitabine of formula 1, comprising the steps of:
- (1) hydrolyzing a methylacetonide compound of formula 2 to obtain a triol compound of formula 3;
- (2) reacting the compound of formula 3 with an haloalkyl formate of formula 4 in the presence of mixture of pyridine and triethylamine to obtain a β-anomer-rich trialkyl carbonate compound of formula 5;
- (3) conducting a glycosylation of the compound of formula 5 using 5-fluorocytosine in the presence of an acid to obtain a dialkoxycarbonyl cytidine compound of formula 6;
- (4) performing carbamoylation of the compound of formula 6 using n-pentyl chloroformate to obtain a carbamoylcytidine compound of formula 7;
- and
- (5) deprotecting the carbonate hydroxy protecting groups of the compound of formula 7:
- wherein,
- X is chloro, bromo or iodo;
- and
- R is methyl or ethyl.
7 more elements
Dependencies are inferred from the claim text.