Processes and intermediates for making sweet taste enhancers
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.
1. A process of preparing a compound having structural Formula (I):
comprising
i) reacting a compound having structural Formula (IIIa)
with NH 2 S(O) 2 NH 2 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 —NH 2 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.
2. The process of claim 1 , comprising reacting the compound having structural Formula (IIIa) with NH 2 —S(O) 2 —NH 2 in the presence of a base to provide the compound of Formula (I).
3. The process of claim 1 , comprising reacting the compound having structural Formula (IIIa) with Cl—S(O) 2 —NH 2 to provide the compound having structural Formula (IIb) which is further reacted with a base to provide the compound having structural Formula (I).
4. 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.
5. 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 C 1 -C 12 alkylene or C 1 -C 12 alkenylene; and R 8 is C 1 -C 12 alkyl.
6. The process of claim 5 , wherein the mixture is washed with an ether prior to combination with the alcohol.