Processes and intermediates for making sweet taste enhancers
AssigneeSenomyx, Inc.
InventorsCatherine Tachdjian, Donald S. Karanewsky, Xiao-Qing Tang, Qing Chen, Peter Leeming, Tayyab Rashid, Daniel Levin
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Abstract
The present invention includes methods/processes and intermediates for preparing compounds having structural Formula (I): wherein X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl.
Claims11
A compound having structural Formula (IIIc):
- wherein
- R1 is —CN, or —C(O)N(R2)2;
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- R8 is C1-C12 alkyl;
- and
- R2 is C1-C12 alkyl.
A process of preparing a compound having structural Formula (IIIa):
- comprising reducing a compound having structural Formula (IV), or treating a compound having structural Formula (IV) with ammonia,
- wherein
- R4 is nitro or halo;
- and
- X is —Y—C(O)—NHR2,
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- and
- R2 is hydrogen or C1-C12 alkyl.
A compound having structural Formula (IV):
- wherein
- R4 is nitro, —NH2, or halo;
- and
- X is —Y—C(O)—NHR2,
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- and
- R2 is hydrogen or C1-C12 alkyl.
A process of preparing a compound having structural Formula (IIIc):
- comprising reacting a compound having structural Formula (X)
- with R8—NH2, in the presence of an activating reagent;
- wherein
- R1 is —CN or —C(O)NH2;
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- and
- R8 is C1-C12 alkyl;
- and
- R9 is hydrogen or C1-C12 alkyl.
A process of preparing a compound having structural Formula (IIIc1):
- comprising reacting HO—Y—C(O)—NHR8 with
- in the presence of a base to form a first mixture solution,
- concentrating the first mixture solution to form a concentrated first mixture solution,
- wherein the volume of the concentrated first mixture solution is equivalent to or less than
- about 50% of the volume of the first mixture solution,
- diluting the concentrated first mixture solution with an ether to form a second mixture solution,
- concentrating the second mixture solution to form a concentrated second mixture solution, wherein the volume of the concentrated second mixture solution is equivalent to or
- less than about 50% of the volume of the second mixture solution,
- diluting the concentrated second mixture solution with ethyl acetate to form a third mixture solution, and
- concentrating the third mixture solution to form a concentrated third mixture solution,
- wherein the compound having structural Formula (IIIc1) precipitates as a solid;
- wherein
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- and
- R8 is C1-C12 alkyl.
Dependencies are inferred from the claim text.