Antifungal Compound Process
AssigneeMycovia Pharmaceuticals, Inc.
InventorsDavid Dale WIRTH, Christopher M. YATES, William J. HOEKSTRA, Martin F. BINDL, Eduard HARTMANN
Life of this patent
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Abstract
The present invention relates to a process for preparing a compound of 5 or 5*, or a mixture thereof, that is useful as an antifungal agent. In particular, the invention seeks to provide new methodology for preparing compounds 7, 7* and 11, 11* and substituted derivatives thereof.
Claims43
A process to prepare a compound of Formula 1 or 1*, or mixture thereof:
- the process comprising reacting a compound of Formula 2:
- with nitromethane in the presence of a chiral catalyst of Formula 3:
- wherein R4 is H, optionally substituted alkyl, (C═O)-optionally substituted alkyl, (C═O)-optionally substituted aryl;
- and R5 is H, optionally substituted alkyl, optionally substituted arylalkyl, or optionally substituted aryl;
- to provide a compound of Formula 1 or 1*, or mixture thereof;
- wherein each R is independently halo, —O(C═O)-alkyl, —O(C═O)-substituted alkyl, —O(C═O)-aryl, —O(C═O)-substituted aryl, —O(C═O)—O-alkyl, —O(C═O)—O-substituted alkyl, —O(C═O)—O-aryl, —O(C═O)—O-substituted aryl, —O(SO2)-alkyl, —O(SO2)-substituted alkyl, —O(SO2)-aryl, —O(SO2)-substituted aryl,
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12-14. (canceled)
16-17. (canceled)
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A process to prepare a compound of Formula 5 or 5*, or mixture thereof:
- the method comprising:
- (a) reacting a compound of Formula 6:
- with nitromethane in the presence of a chiral catalyst of Formula 3:
- to provide a compound of Formula 7 or 7*, or mixture thereof;
- and
- (b) conversion of a compound of Formula 7 or 7*, or mixture thereof, to a compound of Formula 5 or 5*, or mixture thereof;
- wherein each R2 is independently OCF3 or OCH2CF3;
- each R3 is independently halo, —O(C═O)-alkyl, —O(C═O)-substituted alkyl, —O(C═O)-aryl, —O(C═O)-substituted aryl, —O(C═O)—O-alkyl, —O(C═O)—O-substituted alkyl, —O(C═O)—O-aryl, —O(C═O)—O-substituted aryl, —O(SO2)-alkyl, —O(SO2)-substituted alkyl, —O(SO2)-aryl, or —O(SO2)-substituted aryl;
- each R4 is H, optionally substituted alkyl, (C═O)-optionally substituted alkyl, (C═O)-optionally substituted aryl;
- and R5 is H, optionally substituted alkyl, optionally substituted arylalkyl, or optionally substituted aryl.
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48-49. (canceled)
Dependencies are inferred from the claim text.