4’-Azido-3’-O-benzoyl-5’-O-(m-chlorobenzoyl)-2’-deoxy-2’-fluoro-beta-D-arabinouridine synthesis
- Product Name:4’-Azido-3’-O-benzoyl-5’-O-(m-chlorobenzoyl)-2’-deoxy-2’-fluoro-beta-D-arabinouridine
- CAS Number:1333126-30-9
- Molecular formula:C23H17ClFN5O7
- Molecular Weight:529.87
![2,4(1H,3H)-Pyrimidinedione, 1-[4-C-azido-2,5-dideoxy-2-fluoro-5-iodo-β-D-arabinofuranosyl]-](/CAS/20211123/GIF/173379-67-4.gif)
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Yield:1333126-30-9 71.3%
Reaction Conditions:
in N,N-dimethyl-formamide at 20; for 8 h;
Steps:
1
Example 1 [0028] The key intermediate compound 3 of the pyrimidine nucleoside derivatives encompassed in the invention can be synthesized according the following procedure: the synthesis of the key intermediate 2′-deoxy-2′-β-fluoro-4′-azido-3′-O-benzoyl-5′-O-(m-chlorobenzoyl)uridine (3) can be found in the description of CN 100532388C. The present invention has modified the last two steps of the synthesis process to be as follows: adding benzoyl chloride with stirring to compound 1 dissolved in DMF followed by the addition of mCPBA/mCBA separately, reacting in room temperature for 8 h before filtration, removing the solvent under reduced pressure (below 50° C.) and purifying with column chromatography to give compound 3 (71.3%). Reference can be made to Scheme A.
References:
US2013/303747,2013,A1 Location in patent:Paragraph 0028
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