Process for preparing alkyl pyroglutamic acids

A composition comprising at least two compounds selected from the compounds of formula (II):

• or acceptable salts, hydrates, or solvates thereof;
• wherein
• R5 is hydrogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, M+, or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped;
• where M+ is a cation forming a salt;
• R6 is unbranched or branched C2-C24 alkyl, unbranched or branched C2-C24 alkenyl, unbranched or branched C2-C24 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl(C1-C6 alkyl), each optionally substituted with one or more of R7, and
• wherein R7 is halogen, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CO2H, —CO2(C1-C6 alkyl), —CON(C1-C6 alkyl), —CON(C1-C6 alkyl)2, C3-C8 cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CO2H, —CO2(C1-C6 alkyl), —CON(C1-C6 alkyl),
• or —CON(C1-C6 alkyl)2, and
• of formula (III):
• or acceptable salts, hydrates, or solvates thereof;
• wherein
• each R8 is independently hydrogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, M+, or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and where the polyoxyalkylene moiety is capped or uncapped;
• where M+ is a cation forming a salt;
• R9 is unbranched or branched C2-C24 alkyl, unbranched or branched C2-C24 alkenyl, unbranched or branched C2-C24 alkynyl, O3—C8 cycloalkyl, or C3-C8 cycloalkyl(C1-C6 alkyl), each optionally substituted with one or more of R10;
• and
• wherein R10 is halogen, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CO2H, —CO2(C1-C6 alkyl), —CON(C1-C6 alkyl), —CON(C1-C6 alkyl)2, C3-C8 cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CO2H, —CO2(C1-C6 alkyl), —CON(C1-C6 alkyl),
• or —CON(C1-C6 alkyl)2.

A method of preparing a compound of formula (IV) or a mixture of one or more compounds of formula (IV):

• or acceptable salts, hydrates, or solvates thereof;
• wherein
• R11 is hydrogen, C1-C6 alkyl, C1-C6 hydroxyalkyl, M+, or a polyoxyalkylene moiety having oxyalkyl groups that are the same or different, and can be capped or uncapped;
• where M+ is a cation forming a salt;
• R12 is unbranched or branched C3-C24 alkyl, unbranched or branched C3-C24 alkenyl, or unbranched or branched C3-C24 alkynyl, each optionally substituted with one or more of R15;
• and
• wherein R15 is halogen, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CO2H, —CO2(C1-C6 alkyl), —CON(C1-C6 alkyl), —CON(C1-C6 alkyl)2, C3-C8 cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein each cycloalkyl, aryl, heteroaryl, and heterocyclyl are optionally substituted with one or more of halogen, —CN, C1-C6 alkyl, C1-C6 haloalkyl, —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2, —OH, C1-C6 alkoxy, C1-C6 haloalkoxy, —CO2H, —CO2(C1-C6 alkyl), —CON(C1-C6 alkyl),
• or —CON(C1-C6 alkyl)2;
• comprising
• treating a glutamate of formula:
• wherein each R14 is independently selected form hydrogen, M+, C1-C6 alkyl, C1-C6 hydroxyalkyl, —(C1-C6 alkyl-0)1-4H, aryl, aryl(C1-C6 alkyl), or polyoxyalkylene unit;
• with an aldehyde of formula:
• wherein R13 is C1-C23 alkyl, C2-C23 alkenyl, or C2-C23 alkynyl, each optionally substituted with one or more of R15.