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US 10,087,154 B2Granted
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.
Claims6
A process of preparing a compound having structural Formula (I):
- comprising
- i) reacting a compound having structural Formula (IIIa)
- with NH2S(O)2NH2 in the presence of a base to provide the compound having structural Formula (I), or
- ii) reacting the compound having structural Formula (IIIa) with Cl—S(O)2—NH2 to provide a compound having structural Formula (IIb)
- which is further reacted with a base to provide the compound having structural Formula (I),
- wherein X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, or substituted heteroalkenyl.
3 more elements
A process of preparing a compound having structural Formula (lb):
- comprising reacting a compound having structural Formula (I)
- with an alkali metal-based inorganic base,
- wherein
- M is a cation of sodium;
- X is alkyl, substituted alkyl, alkenyl, substituted alkenyl, heteroalkyl, substituted heteroalkyl, heteroalkenyl, substituted heteroalkenyl;
- and
- n is 1.
4 more elements
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° C. to about 95° C. to provide a mixture,
- combining an alcohol with the mixture to form an aqueous-alcohol mixture having a pH,
- combining a hydrochloride solution with the aqueous-alcohol mixture to adjust the pH thereof to a range from about 4 to about 5,
- wherein:
- Y is C1-C12 alkylene or C1-C12 alkenylene;
- and R8 is C1-C12 alkyl.
5 more elements
Dependencies are inferred from the claim text.