US 12,110,523 B2
Reagents and methods for esterification
Ronald T. Raines, Madison, WI (US); and Kalie Mix, Madison, WI (US)
Assigned to Wisconsin Alumni Research Foundation, Madison, WI (US)
Filed by Wisconsin Alumni Research Foundation, Madison, WI (US)
Filed on Nov. 15, 2021, as Appl. No. 17/526,816.
Application 16/588,224 is a division of application No. 15/730,197, filed on Oct. 11, 2017, granted, now 10,428,323, issued on Oct. 1, 2019.
Application 15/730,197 is a division of application No. 15/093,510, filed on Apr. 7, 2016, granted, now 9,790,483, issued on Oct. 17, 2017.
Application 17/526,816 is a continuation of application No. 16/588,224, filed on Sep. 30, 2019, granted, now 11,180,748.
Claims priority of provisional application 62/319,153, filed on Apr. 6, 2016.
Claims priority of provisional application 62/145,193, filed on Apr. 9, 2015.
Prior Publication US 2022/0073899 A1, Mar. 10, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 231/12 (2006.01); C07C 245/18 (2006.01); C07C 269/06 (2006.01); C07C 319/12 (2006.01); C07D 207/46 (2006.01); C07K 1/13 (2006.01); C12N 9/96 (2006.01)
CPC C12N 9/96 (2013.01) [C07C 231/12 (2013.01); C07C 245/18 (2013.01); C07C 269/06 (2013.01); C07C 319/12 (2013.01); C07D 207/46 (2013.01); C07K 1/13 (2013.01)] 24 Claims
 
1. A compound of formula I:

OG Complex Work Unit Chemistry
or salts thereof,
where:
R is hydrogen, an alkyl group, alkenyl group, or an alkynyl group;
RM is M or -L-M, where M is a polymer or a non-polymeric organic group, having from 1 to 100 carbon atoms and optionally nitrogen, oxygen or sulfur atoms, and -L is a divalent linker moiety having from 1-30 carbon atoms and optionally nitrogen, oxygen or sulfur atoms; and
RA represents 1 to 3 non-hydrogen substituents on the phenyl ring, wherein the non-hydrogen substituents are selected from the group consisting of alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, arylalkyl, haloalkyl, haloalkoxy, heterocyclyl and RP—CO—NH—, where the alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, arylalkyl and heterocyclyl groups are optionally substituted;
wherein optional substitution is substitution with one or more groups selected from oxo, thiox, -sulfhydryl, hydroxy, alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, aryl, aryloxy, heteroaryl, heteroaryloxy, carbocyclyl, carbocyclyloxy, heterocyclyl, heterocyclyloxy, alkylthio, alkenylthio, alkynylthio, arylthio, thioheteroaryl, thiocarbocyclyl, thioheterocyclyl, —CORs, —COH, —OCORs, —OCOH, —CO—ORs, —CO—OH, —CO—O—CO-Rs, —CON(Rs)2, —CONHRs, —CONH2, —NRs-CORs, —NHCORs, —NHRs, —N(Rs)2, —O—SO2-Rs, —SO2-Rs, —SO2—NHRs, —SO2—N(Rs)2, —NRs-SO2-Rs, —NH—SO2-Rs, —NRsCO—N(Rs)2, —NH—CO—NHRs, —O—PO(ORs)2, —O—PO(ORs)(N(Rs)2), —O—PO(N(Rs)2)2, —N—PO(ORs)2, —N—PO(ORs)(N(Rs)2), —P(Rs)2, —B(OH)2, —B(OH)(ORs), and —B(ORs)2, where each Rs independently is an alkyl, alkenyl, alkynyl, aryl, heteroaryl, carbocyclyl, or heterocyclyl group or two Rs within the same substituent can together form a carbocyclic or heterocyclic ring having 3 to 10 ring atoms.