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US 10,590,092 B2Granted
Process for the manufacture of isavuconazole or ravuconazole
AssigneeBasilea Pharmaceutica AG
InventorsRuben Van Summeren, Harrie Vaessen, Daniel Mink, Mario Waser
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Abstract
The invention relates to a process for the manufacture of diastereomerically and enantiomerically enriched triazole compounds isavuconazole and ravuconazole, comprising a Reformatsky reaction between a ketone and a 2-halozincpropionate ester, followed by a resolution step, preferably an enzymatic resolution with an esterase enzyme.
Claims3
A mixture of 3-Hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-3-phenyl-butyric acid ester diastereomers of formula (I):
- comprising the racemic mixture of (2R,3R)/(2S,3S) esters at a diastereomeric excess, as determined by GC, between 97% and 99.9%, wherein R1 is fluoro, R2 is hydrogen and R is a C1-C12alkyl, a C5-C12aryl or a C6-C11aralkyl.
A (2R,3R)-3-Hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-3-phenyl-butyric acid ester derivative according to formula (I):
- (R,R-Ester I)
- wherein
- R is a C1-C12 alkyl or C5-C12aryl,
- R1 is fluoro and
- R2 is hydrogen.
2 more elements
Dependencies are inferred from the claim text.