IP Library Granted Patent US 8,647,882
Granted Patent B2
US 8,647,882 · App. 13/241,767 · Granted Feb 11, 2014

Chiral selectors and stationary phases for separating enantiomer mixtures

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Quick Facts
Patent No.
US 8,647,882
App. No.
13/241,767
Granted
Feb 11, 2014
Kind
B2
Abstract

Chiral selectors having α-unsubstituted β-amino acid derivatives of the structure: a stationary phase for separating substance mixtures containing the chiral selector, and processes for separating mixtures of chiral substances, including enantiomers, and especially enantiomers of substances selected from β-amino acids and derivatives thereof, α-amino acids and α-hydroxy acids are provided.

Claims (28)

1. A stationary phase for chromatographic separation, comprising

a support material, and

a chiral selector covalently attached to the support material;

wherein

the support material comprises silica gel or a monolith, and

the chiral selector comprises: an α-unsubstituted β-amino acid derivative of structure (I):

wherein

n is an integer of 1-5,

R 1 is —(C 6 -C 10 )-aryl, (C 7 -C 13 )-aralkyl, (C 7 -C 10 )-heteroaralkyl, pyridyl,

X is a linking group covalently attached to the support material,

R 2 is 3,5-dinitrobenzoyl or naphthyl, and

the chiral selector is present in predominantly one absolute configuration with respect to the C-3 carbon atom (β-carbon atom).

2. The stationary phase for chromatographic separation according to claim 1 , wherein R 1 is phenyl.

3. The stationary phase for chromatographic separation according to claim 1 , wherein X is an aminoalkyl linker and the chiral selector is bonded to the support material as a carboxamide formed of the C1 carbon and amine nitrogen of the aminoalkyl linker.

4. A process for chromatographically separating a substance mixture, comprising:

contacting a solution of the substance mixture to be separated with the stationary phase for chromatographic separation according to claim 1 ;

passing a mobile phase through the stationary phase to effect separation of mixture components on the basis of their different interaction with the stationary phase, and optionally,

isolating the separated components from the mobile phase, detecting the separated components or detecting and quantifying the components;

wherein

the substance mixture comprises a mixture of chiral substances.

5. The process for chromatographically separating a substance mixture according to claim 4 , wherein the substance mixture comprises trace amounts of enantiomers.

6. The process for chromatographically separating a substance mixture according to claim 5 , wherein the enantiomers comprise enantiomers of α- and β-amino acids.

7. A high pressure liquid chromatography process comprising:

contacting a solution of the substance mixture to be separated with the stationary phase for chromatographic separation according to claim 1 ;

passing a mobile phase through the stationary phase to effect separation of mixture components on the basis of their different interaction with the stationary phase;

detecting the separated components; and

quantifying the components;

wherein the substance mixture comprises enantiomers of at least one material selected from the group consisting of α-amino acids, β-amino acids, α-hydroxy acids and derivatives thereof.

Assignments (1)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →