Synthesis of isotopically labeled alpha-keto acids and esters
AssigneeSpectra Gases, Inc.
InventorsRodolfo Antonio Martinez, Mark Minton, Frank Elbert Anderson, Erick Gabriel Ortiz, Kenneth Edmund Tortolani
Life of this patent
Estimating the term…
Abstract
Isotopically labeled alpha-keto acids and esters are disclosed herein. Also disclosed are methods of synthesizing isotopically labeled alpha-keto acids and esters.
Claims44
A process for preparing an isotopically labeled compound of Formula (IIIa)
- comprising reacting a compound having Formula (IIIa′)
- with a base and R2X,
- wherein X is F, Cl, Br or I;
- and
- R2 is a C1-C36 substituted or unsubstituted, saturated, or unsaturated, linear, branched, cyclic, aromatic, or substituted aromatic group, wherein R2 may include a heteroatom including O, N, S, Si, and P wherein any of the carbon atoms or heteroatoms may be isotopically labeled.
A process of forming an isotopically labeled compound of Formula (V)
- comprising hydrogenating a compound of Formula (IIIb)
A process for the preparation of an isotopically labeled compound of Formula (IIIa′)
- comprising reacting a compound of Formula (IIb)
- with carbon dioxide in a solvent.
A process for the preparation of an isotopically labeled compound of Formula (IIb)
- comprising reacting a compound of Formula (IIa)
- with magnesium in a solvent.
A process for the preparation of an isotopically labeled pyruvic acid analog having Formula (V)
- comprising the steps of:
- a) reacting a compound of Formula (IIa)
- with magnesium in a solvent to yield the Grignard having Formula (IIb)
- b) reacting said compound of Formula (IIb) with carbon dioxide in a solvent to yield a compound of Formula (IIIa′)
- c) reacting said compound of Formula (IIIa′)) with a weak base and R2X to yield a compound of Formula (IIIa), wherein X is F, Cl, Br or I;
- and
- R2 is a C1-C36 substituted or unsubstituted, saturated, or unsaturated, linear, branched, cyclic, aromatic, or substituted aromatic group, wherein R2 may include a heteroatom including O, N. S, Si, and P wherein any of the carbon atoms or heteroatoms may be isotopically labeled;
- d) reacting said compound of Formula (IIIa) with ozone in a solvent to yield the compound of Formula (IIIb);
- e) hydrogenating said compound of Formula (IIIb) to form said isotopically labeled pryuvic acid analog.
A process for preparing an isotopically labeled compound of Formula (IV)
- comprising:
- a) reacting a compound of Formula (IIIa′) with oxalyl chloride to form an intermediate of Formula (VI)
- b) reacting said intermediate with an amide in a solvent to form said compound of Formula (IV).
Dependencies are inferred from the claim text.