Granted Patent B2

US 12,428,388 · App. 18/754,049 · Granted Sep 30, 2025

Inventors: Alexander A. Gall (Bothell, WA); Ivan Baraznenok (Bothell, WA)

Assignee: Cepheid

C07D307/20C11D1/72

Abstract

Claims (28)

1. A method of preparing of a compound of Formula (I):

or a stereoisomer, a hydrate, or a solvate thereof,

wherein:

R is an optionally substituted C 6 -C 70 alkyl or optionally substituted C 6 -C 70 alkenyl;

w is an integer ranging from 0 to 20,

x is an integer ranging from 0 to 20,

y is an integer ranging from 0 to 20, and

z is an integer ranging from 1 to 20,

comprising the steps of:

(a) forming a trimethylsilyl protected derivative of a compound of formula (II):

and

(b) contacting the trimethylsilyl protected derivative of the compound of formula (II) with a reducing agent and gallium tribromide, optionally in a solvent.

2. The method of claim 1 , wherein forming a trimethylsilyl derivative of compound of Formula (II) is done by contacting a compound of Formula (II) with a silylating agent in a solvent.

3. The method of claim 1 , wherein the silylating agent is hexamethyldisilazane (HMDS).

4. The method of claim 1 , wherein the reducing agent is 1,1,3,3-tetramethyldisiloxane.

5. The method of claim 1 , wherein step (b) is performed at a temperature ranging from about 25° C. to about 80° C.

6. The method of claim 1 , wherein step (b) does not require a solvent.

7. The method of claim 1 , further comprising contacting the product of step (b) with water.

8. The method of claim 1 , wherein R is an unsubstituted C 6 -C 50 alkyl or unsubstituted C 6 -C 50 alkenyl.

9. The method of claim 1 , wherein R is an unsubstituted C 10 -C 25 alkyl or unsubstituted C 10 -C 25 alkenyl.

10. The method of claim 1 , wherein the sum of w, x, y, and z is 20.

11. The method of claim 1 , wherein the compound is represented by Formula (IA):

or a stereoisomer, a hydrate, or a solvate thereof.

12. The method of claim 1 , wherein R is n-decyl, n-undecyl, n-dodecyl, n-hexadecyl, or n-heptadecyl.

13. The method of claim 1 , wherein the compound is:

or an stereoisomer, solvate, or hydrate thereof, wherein w+x+y+z=20.

14. The method of claim 1 , wherein the compound of Formula (I) is

or a stereoisomer, solvate, or hydrate thereof, wherein w+x+y+z=20.

Assignments (1)

Continuity (3)

References Cited (16)