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New chiral columns with broad chiral selectivity

A chiral stationary phase and compound technology, applied in the field of chiral chemistry, can solve problems such as aggravated separation of enantiomers

Inactive Publication Date: 2007-10-10
VANDERBILT UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem of separating enantiomers is further exacerbated by the fact that conventional synthetic techniques almost always result in a mixture of enantiomers
[0015] In the past, a large number of chiral columns have been fabricated; however, only a few exhibit broad chiral selectivity

Method used

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  • New chiral columns with broad chiral selectivity
  • New chiral columns with broad chiral selectivity
  • New chiral columns with broad chiral selectivity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: Preparation of chiral stationary phase Fmoc-Pro-(Me)Ahx-APS (CSPI)

[0042] To 0.80 g of (Me)Ahx-APS silica (surface (Me)Ahx concentration is 0.64 mmol / g) was added Fmoc-Pro-OH (3 eq., 0.52 g) in 8 mL DMF, HATU (3 eq. , 0.58 g) and DIPEA (3 equiv, 0.20 g). After stirring for 6 hours, the resulting silica was collected by filtration and washed with DMF, methanol and DCM to obtain the desired chiral stationary phase. The surface Pro concentration was determined to be 0.57 mmol / g according to the Fmoc split method. The resulting chiral stationary phase was loaded into a 50 x 4.6 mm HPLC column using the standard homogenate packing method.

Embodiment 2

[0043] Embodiment 2: the preparation of chiral stationary phase Fmoc-Pr02-(Me)Ahx-APS (CSP2)

[0044] To 0.80 g of (Me)Ahx-APS silica (surface (Me)Ahx concentration is 0.64 mmol / g) was added Fmoc-Pro-OH (3 eq., 0.52 g) in 8 mL DMF, HATU (3 eq. , 0.58 g) and DIPEA (3 equiv, 0.20 g). After stirring for 6 hours, the resulting silica was collected by filtration and washed with DMF, methanol and DCM. The surface Pro concentration was determined to be 0.55 mmol / g according to the Fmoc split method. The Fmoc protecting group was then removed by treatment with silica in DMF containing 10 mL of 20% (V / V) piperidine for 1 hour. The deprotected silica Pro-(Me)Ahx-APS was collected by filtration and washed with DMF, methanol and DCM. Another module, Fmoc-Pro-OH, was then incorporated onto the resulting silica after the same sequence of reactions to obtain the desired chiral selector on silica. The surface Fmoc concentration was determined to be 0.52 mmol / g according to the Fmoc splitt...

Embodiment 3

[0045] Example 3: Preparation of chiral stationary phase Fmoc-Pro4-(Me)Ahx-APS(CSP3)

[0046] To Rink acidic resin (100-200 mesh, 3.0 g, 0.43 mmol / g) pre-swelled with DCM (20 mL, 30 min) was added Fmoc-(Me )A mixture of Ahx-OH (1.42g, 3.87mmol), DMAP (0.16g, 1.29mmol), NMM (0.39g, 3.87mmol), and DIC (0.49g, 3.87mmol). After stirring for 6 hours, the resin was collected by filtration and washed with DMF, DCM and methanol (20 mL x 3). The Fmoc protecting group was removed by treatment with 20 mL of 20% (V / V) piperidine in DMF for 30 minutes. The deprotected (Me)Ahx-O-Rink resin was collected and washed with DMF, DCM and methanol (20 mL x 3).

[0047] To (Me)Ahx-O-Rink resin was added Fmoc-Pro-OH (1.31 g, 3.87 mmol), HATU (1.47 g, 3.87 mmol), and DIPEA (0.50 g, 3.87 mmol) in 20 mL of anhydrous DMF mixture. After stirring for 3 hours, the resin was filtered and washed with DMF, DCM and methanol (20 mL x 3).

[0048] Then the Fmoc group was removed, and the second, third and f...

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Abstract

A general chiral column with a multiple proline-based chiral stationary phase.

Description

[0001] governmental support [0002] This invention is related to grant numbers NIH 1R01GM63812-01 and NIH1 R01 GM60637-01A1 from the National Institutes of Health. The US Government has rights in this invention. field of invention [0003] The present invention relates to the field of chiral chemistry. More specifically, the present invention relates to the separation of enantiomers, ie isomers in which the atoms or groups are arranged such that the two molecules are not superimposable. [0004] The present inventors have developed a new class of chiral columns, which can resolve a large number of racemic compounds. These columns are stable and can be used with a wide variety of mobile phase solvents. Background of the invention [0005] Stereoisomers are molecules that differ from each other only in the orientation of their atoms in space. Stereoisomers are generally classified as diastereomers or enantiomers; the latter include molecules that are mirror images of each...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K17/00C07K17/14
CPCC07K17/14C07K1/22C07K17/00
Inventor T・李
Owner VANDERBILT UNIV
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