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US 12,435,049 B2Granted
Synthesis of vinylic protected alcohol intermediates
AssigneeAmgen Inc.
InventorsAustin G. Smith, Liang Huang
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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 D, wherein OPG and R1 are described herein. Compound D can be useful in synthesizing compound A1, or a salt of solvate thereof, and compound A2, or a salt of solvate thereof.
Claims39
A process for synthesizing compound D:
- comprising:
- (a) admixing compound B, or a salt thereof, and compound C in an organic solvent to form a slurry, wherein the organic solvent is selected from the group consisting of a nonpolar aromatic solvent, an ether solvent, a chlorinated solvent, an alcohol solvent, acetonitrile, dimethylformamide (DMF), dimethylcarbonate, dimethylacetamide (DMAc), N-methylpyrrolidinone (NMP), and a combination thereof:
- and
- (b) admixing the slurry of step (a) and a reducing agent to form a mixture comprising compound D;
- wherein:
- OPG is an alcohol protecting group selected from the group consisting of an ether, an acetal or ketal, an acyl, a sulfonyl, and a silyl ether;
- R1 is H or C1-6alkyl;
- and
- R2 is a protected aldehyde.
6 more elements
Dependencies are inferred from the claim text.