IP Library Granted Patent US 8,247,234
Granted Patent B2
US 8,247,234 · App. 13/151,755 · Granted Aug 21, 2012

Isotopically labeled compositions and method

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Quick Facts
Patent No.
US 8,247,234
App. No.
13/151,755
Granted
Aug 21, 2012
Kind
B2
Abstract

Compounds having stable isotopes 13 C and/or 2 H were synthesized from precursor compositions having solid phase supports or affinity tags.

Claims (18)

1. A method for synthesizing an isotopically enriched compound, comprising:

forming a composition comprised of the formula

A-D-E-C(TXZ)

wherein A is a support selected from the group consisting of a polymer support, a resin support, a metal support, a nanoparticle support, a magnetic bead support, a silica support, a silicon support, a glass support, a ceramic support, and a core-shell compound support;

wherein D comprises aryl having 6-10 ring atoms and an oxygen atom attached to A;

wherein E is selected from the group consisting of sulfur, sulfoxide, sulfone, selenium, selenoxide, or selenone;

wherein T, X, and Z comprise groups each independently chosen from 1 H, 2 H, a C 1 -C 4 alkyl, fluoro, chloro, bromo, iodo, amino, NHR, NR 2 , and OR;

wherein R comprises C 1 -C 4 alkyl, chloro, bromo, amino, a monocyclic aryl, substituted monocyclic aryl, bicyclic aryl, and substituted bicyclic aryl; and

wherein at least one of C, T, X, and Z groups comprises a stable isotope, wherein the stable isotope of C is 13 C and wherein the stable isotope of T, X, Z comprises 13 C or 2 H; and

subjecting the composition to conditions whereby —C(TXZ) detaches from E and becomes part of an isotopically labeled compound.

2. The method of claim 1 , wherein aryl having an oxygen of D comprises monocyclic aryloxy, functionalized monocyclic aryloxy, bicyclic aryloxy, functionalized bicyclic aryloxy,

wherein functionalized monocyclic aryloxy, and functionalized bicyclic aryloxy comprise a substituent chosen from alkyl, haloalkyl, cycloalkyl, halo, nitro, cyano, —OM, and —COOQ, wherein M is chosen from hydrogen, alkyl, haloalkyl, cycloalkyl, phenyl, and substituted phenyl, and wherein Q is chosen from hydrogen and alkyl.

3. The method of claim 1 , wherein E is sulfur, sulfoxide, or sulfone; wherein C is 13 C; and wherein at least one of T, X, and Z is 2 H.

4. The method of claim 1 , wherein haloalkyl comprises fluoroalkyl, bromoalkyl, chloroalkyl, and iodoalkyl.

5. The method of claim 1 , wherein T, X, and Z comprise monocyclic aryl, monocyclic aryloxy, functionalized monocyclic aryloxy, bicyclic aryl, bicyclic aryloxy, functionalized bicyclic aryloxy,

wherein functionalized monocyclic aryl, functionalized monocyclic aryloxy, functionalized bicyclic aryl, and functionalized bicyclic aryloxy comprise a substituent chosen from alkyl, haloalkyl, cycloalkyl, halo, nitro, cyano, —OM, and —COOQ, wherein M is chosen from hydrogen, alkyl, haloalkyl, cycloalkyl, phenyl, and substituted phenyl, and wherein Q is chosen from hydrogen and alkyl.

6. The method of claim 1 , wherein said resin support is selected from polystyrene and resin-bound thiophenol crosslinked with divinylbenzene.

7. The method of claim 1 wherein group D is 1,4-disubstituted aryl having an oxygen attached to group A, wherein group E is selected from sulfur, sulfoxide, and sulfone.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2018
From: LOS ALAMOS NATIONAL SECURITY, LLC
To: TRIAD NATIONAL SECURITY, LLC
Reel/Frame 048007/0874 →