Processes and intermediates for making sweet taste enhancers

Patent metadata

Field	Value
Publication number	US-10087154-B2
Application number	US-201715664179-A
Country	US
Kind code	B2
Filing date	Jul 31, 2017
Priority date	Jul 31, 2008
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

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.

First claim

What is claimed is:

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.

Assignees

• Senomyx Inc

Inventors

• Tachdjian Catherine
• Karanewsky Donald S
• Tang Xiao-Qing
• Chen Qing
• Leeming Peter
• Rashid Tayyab
• Levin Daniel

Classifications

• C07D285/16 Primary

  Thiadiazines; Hydrogenated thiadiazines · CPC title

• C07C237/44

  having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title

• C01B21/096

  Amidosulfonic acid; Salts thereof · CPC title

• C07C307/10

  having nitrogen atoms of the sulfamide groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C253/30

  by reactions not involving the formation of cyano groups · CPC title