Proline chiral columns with broad chiral selectivity

• US 20050092686A1
• Filed: 11/12/2004
• Published: 05/05/2005
• Est. Priority Date: 04/28/2003
• Status: Active Grant

• Current Assignee: Tingyu Li
• Original Assignee: Tingyu Li
• Inventors: Li, Tingyu
• Granted Patent: US 7,160,449 B2
• Time in Patent Office: Days
• US Class Current: 210/656
• CPC Class Codes: B01D 15/3833 Chiral chromatography
• CPC Class Codes: B01J 20/289 bonded via a spacer
• CPC Class Codes: B01J 20/29 Chiral phases
• CPC Class Codes: B01J 20/3242 Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
• CPC Class Codes: C02F 1/42 by ion-exchange ion-exchange in general B01J

Abstract

A general chiral column with a multipleproline-based chiral stationary phase. Embodiments include chiral stationary phases of the following formula: wherein n is any integer of 2 or greater, and analogs and isomers thereof.

Claims

1. A chiral stationary phase compound of the following formula:

2. The chiral stationary phase compound of claim 1, wherein n is any integer from 2 to 10.

3. The chiral stationary phase compound of claim 1, wherein the support is a silica support.

4. The chiral stationary phase compound of claim 1, wherein the linker is a disubstituted amino group.

5. The chiral stationary phase compound of claim 4, wherein the linker is an N-methylamino group.

6. The chiral stationary phase compound of claim 4, wherein the linker is a 6-methylaminohexanoic acid group.

7. The chiral stationary phase of a compound of claim 1, wherein the end-capping group is a Piv, Fmoc, Boc, Cbz, Aca, Tapa, Dmb, or a Tpa group.

8. The chiral stationary phase of claim 1, wherein the linker is of the following formula:

9. The chiral stationary phase compound of claim 1, wherein the linker is of the following formula:

10. The chiral stationary phase compound of claim 1, wherein the end-capping group is a Piv, Fmoc, Boc group.

11. The chiral stationary phase compound of claim 1, of the following formula:

18. A chiral stationary phase compound of claim 1, of the following formula:

Fmoc-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica (CSP2);

Fmoc-Pro-Pro-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica (CSP3);

Fmoc-Pro-Pro-Pro-Pro-Pro-Pro-(Me)N—

(CH₂)₅CO—

NH(CH₂)₃Silica (CSP4);

and analogs and isomers thereof.

12. A chiral selector, of the following formula:

13. A process for separating enantiomeric mixtures by gas chromatography and capillary electrophoresis using a chiral selector of claim 12.

14. An optically active proline derivative of the formula:

15. A process for separating enantiomeric mixtures by liquid chromatography, comprising:

providing a racemic mixture;

providing a chiral column that comprises an optically active multi-proline compound or an analog or isomer thereof; and

introducing the mixture to the chiral column.

16. The process of claim 15, wherein the optically active multi-proline compound is of the following formula:

17. The process of claim 15, wherein the optically active multi-proline compound of of the following formula: