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US 11,498,907 B2Granted
Process of preparing a peptide epoxyketone immunoproteasome inhibitor, and precursors thereof
AssigneeKezar Life Sciences
InventorsHenry Johnson, Sean Dalziel, Dustin McMinn
Life of this patent
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Abstract
Disclosed herein are methods for preparing [(2S,3R)-N-[(2S)-3-(cyclopent-1-en-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[(2S)-2-[2-(morpholin-4-yl)acetamido]propanamido]propanamide (compound “G”): and precursors thereof.
Claims7
A method of preparing (S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-aminium salt (compound “F”)
- comprising:
- (a) admixing trifluoroacetic acid (“TFA”) and tert-butyl-((S)-3-(cyclopent-1-en-1-yl)-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)carbamate (compound “H”):
- in an aprotic solvent at a temperature in a range of −5° C. to 5° C. to form a mixture;
- (b) concentrating the mixture;
- and
- (c) admixing an acid and the concentrated mixture of step (b) at a temperature in a range of −5° C. to 5° C. to form compound F,
- wherein X− is a conjugate base of the acid.
4 more elements
Dependencies are inferred from the claim text.