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.
Claims13
A process of preparing a compound having structural Formula (I):
- comprising reacting a compound having structural Formula (II)
- with a base or an activating reagent,
- wherein
- R1 is —CN or —C(O)NH2;
- and
- X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl.
A process of preparing a compound having structural Formula (I):
- comprising reacting a compound having structural Formula (VII)
- with NH3 or NH3.H2O;
- wherein
- X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl;
- and
- R7 is a leaving group selected from the group consisting of halo, —OMs, —OTs, and —OTf.
A compound having structural Formula (VII):
- wherein
- X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl;
- and
- R7 is a leaving group selected from the group consisting of halo, —OMs, —OTs, and —OTf.
A process of preparing a compound having structural Formula (Ia):
- comprising reacting a compound having structural Formula (VIII)
- with R8—NH2, in the presence of an activating reagent;
- wherein
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- R8 is C1-C12 alkyl;
- and
- R9 is hydrogen or C1-C12 alkyl.
A process of preparing a compound having structural Formula (Ib):
- comprising reacting a compound having structural Formula (I)
- with an alkali metal- or alkaline earth metal-based inorganic base,
- wherein
- M is a cation of alkali metal or alkaline earth metal;
- X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl;
- n is 1, when M is a cation of alkali metal;
- and
- n is 2, when M is a cation of alkaline earth metal.
A process of preparing a compound having structural Formula (Ia):
- comprising
- reacting a compound having structural Formula (IIc1)
- with a hydroxide or alkoxide base in an aqueous solution at a temperature ranging from about 25 to about 95° C.,
- wherein
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- and
- R8 is C1-C12 alkyl.
Dependencies are inferred from the claim text.