Synthesis of vinyl cyclobutyl intermediates
AssigneeAmgen Inc.
InventorsAustin G. SMITH, Michael T. CORBETT, Neil Fred LANGILLE, Kyle D. BAUCOM, Peter K. DORNAN, Gabrielle ST-PIERRE, Philipp C. ROOSEN, Sheng CUI, Roberto PROFETA
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Abstract
Provided herein are processes for synthesizing intermediates useful in preparing Mcl-1 inhibitors. In particular, provided herein are processes for synthesizing compound F, or a salt thereof, wherein R1 and OPG2 are described herein. Compound F can be useful in synthesizing compound A1, or a salt of solvate thereof, and compound A2, or a salt of solvate thereof.
Claims16
1-64. (canceled)
A process for synthesizing compound A1, or a salt or solvate thereof, using compound F:
- wherein
- the process for synthesizing compound F or a salt thereof
- comprises:
- (a) protecting a secondary alcohol of compound B, or a salt thereof, by reacting compound B, or salt thereof, with an alcohol protecting group reagent to form compound C, or a salt thereof:
- (b) removing compound C's acetyl group to form a primary alcohol of compound D, or a salt thereof:
- (c) oxidizing the primary alcohol of compound D, or salt thereof, to form an aldehyde of compound E, or a salt thereof:
- and
- (d) protecting the aldehyde of compound E, or salt thereof, to form a protected aldehyde of compound F, or a salt thereof;
- wherein OPG2 is a secondary alcohol protecting group and R1 is a protected aldehyde.
A process for synthesizing compound A2, or a salt of solvate thereof, using compound F:
- wherein
- the process for synthesizing compound F or a salt thereof
- comprises:
- (a) protecting a secondary alcohol of compound B, or a salt thereof, by reacting compound B, or salt thereof, with an alcohol protecting group reagent to form compound C, or a salt thereof:
- (b) removing compound C's acetyl group to form a primary alcohol of compound D, or a salt thereof:
- (c) oxidizing the primary alcohol of compound D, or salt thereof, to form an aldehyde of compound E, or a salt thereof:
- and
- (d) protecting the aldehyde of compound E, or salt thereof, to form a protected aldehyde of compound F, or a salt thereof;
- wherein OPG2 is a secondary alcohol protecting group and R1 is a protected aldehyde.
A compound having the structure of Formula (I):
- wherein
- R1 is
- or a protected aldehyde;
- R2 is OH or OPG2;
- and
- OPG2 is a secondary alcohol protecting group,
- with the proviso that if R2 is OH, then R1 is
Dependencies are inferred from the claim text.