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New chiral metal complexes and their use for analyzing the chirality of charged compounds by 1h NMR spectroscopy

A metal complex, chemical formula technology, applied in the direction of 3/13 group organic compounds without C-metal bonds, compounds containing periodic table group 3/13 elements, titanium organic compounds, etc.

Active Publication Date: 2018-09-11
KOREA ADVANCED INST OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Until now, even though a variety of chiral solvates have been developed, most of them can only be used to measure the optical purity of specific chiral analytes, thus, it is difficult to apply them to the optical purity of a wider range of chiral analytes. Purity measurement

Method used

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  • New chiral metal complexes and their use for analyzing the chirality of charged compounds by 1h NMR spectroscopy
  • New chiral metal complexes and their use for analyzing the chirality of charged compounds by 1h NMR spectroscopy
  • New chiral metal complexes and their use for analyzing the chirality of charged compounds by 1h NMR spectroscopy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] [Example 1] Preparation of Ligand 1a

[0105]

[0106] Preparation of Compound S1

[0107] (R,R)-1,2-Cyclohexanediamine (1.14 g, 10.0 mmol) was mixed with MeOH (20.0 mL), then 2,2′-dihydroxybenzophenone ( 5.14 g, 24.0 mmol), and stirring was continued at 50° C. for 6 hours. The reaction mixture was filtered and the separated solid was washed with diethyl ether and dried in vacuo to give the title compound S1 (4.41 g, 87%) as a yellow solid.

[0108] 1 H NMR (400MHz, DMSO-d6) δ15.55–15.27(br,2H),9.81(br,2H), 7.39–7.32(m,2H),7.26–7.20(m,2H),7.12–6.81(m ,8H),6.73–6.61(m,4H),3.56–3.45(m,2H),1.88–1.69(m,2H),1.58(br,2H),1.32(br,2H), 1.09(br,2H ); 13 C NMR (100MHz, DMSO-d6) δ171.5, 162.1, 154.0, 132.1, 130.7, 130.5, 128.5, 120.4, 119.5, 119.2, 117.5, 117.2, 115.8, 64.9, 30.9, 23.5; HRMS (EI) m / z calculation C 32 h 30 N 2 o 4 [H] + :507.2278, Measured: 507.2314.

[0109] Preparation of compound 1a

[0110] Compound S1 (2.53 g, 5.00 mmol) was mixed with MeOH (...

Embodiment 2

[0112] [Example 2] Preparation of Ligand 1b

[0113]

[0114] Preparation of Compound S2

[0115] Mix (R,R)-1,2-stilbenediamine (2.12 g, 10.0 mmol) with MeOH (20.0 mL), and then add 2,2′-dihydroxybenzophenone to it while stirring (5.14 g, 24.0 mL), stirring was continued at 50° C. for 12 hours. The reaction mixture was filtered, and the separated solid was washed with ether and dried in vacuo to give the title compound S2 (5.51 g, 91%) as a yellow solid.

[0116] 1 H NMR(400MHz,DMSO-d6)δ15.39-15.32(br,2H),9.40(br,2H),7.31-7.22(m,4H),7.18-6.80(m,14H),6.74-6.50(m ,6H),6.21-6.08(m,2H), 4.95-4.84(m,2H); 13 C NMR (100MHz, DMSO-d6) δ172.8, 161.9, 154.0, 139.8, 132.4, 131.1 130.5, 128.0, 127.7, 127.0, 119.8, 119.5, 118.6, 117.7, 117.5, 117.2, 115.3, 71EI.8; z calculation C 40 h 32 N 2 o 4 [H] + :605.2435, Measured: 605.2476.

[0117] Preparation of compound 1b

[0118] Compound S2 (3.02 g, 5 mmol) was mixed with MeOH (25.0 mL), then NaBH was added in portions at 0 ...

Embodiment 3

[0120] [embodiment 3] the preparation of metal complex Na[Al-1a]

[0121]

[0122] Compound 1a (511 mg, 1.00 mmol) was mixed with MeOH (20.0 mL) to prepare a solution of Compound 1a. NaOH (160 mg, 4.00 mmol) was mixed with MeOH (40.0 mL) to prepare a NaOH solution. NaOH solution and AlCl 3 ·6H 2 O (241mg, 1.00mmol) was added to the solution of compound 1a and stirred at 25°C for 2 hours. The reaction mixture was concentrated under reduced pressure, dissolved in EtOAc, and washed with brine. Na for organic layer 2 SO 4 Dry, filter and concentrate under reduced pressure to give the title compound Na[Al-la] (559 mg, 99%) as an off-white solid.

[0123] 1 H NMR (400MHz, DMSO-d6) δ7.08 (dd, J = 7.5, 1.7Hz, 2H), 6.95-6.86 (m, 4H), 6.78 (ddd, J = 8.1, 7.1, 1.9Hz, 2H), 6.62(dd, J=8.1,1.3 Hz,2H),6.38(td,J=7.3,1.3Hz,2H),6.31(dd,J=8.2,1.2Hz,2H),6.26(td, J=7.2, 1.3Hz, 2H), 4.87(s, 2H), 3.77(d, J=10.2Hz, 2H), 2.48-2.41(m, 2H), 2.23(d, J=12.7Hz, 2H), 1.65(d, J=9.8Hz, 2H), 1.27(...

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Abstract

Provided are novel ligand, a chiral metal complex including the same, and a use of the chiral metal complex for analyzing the chirality of a charged compound by 1H NMR spectroscopy. The chiral metal complex of the present invention may be used as the chiral solvating agent to conveniently analyze the optical purity of charged compounds such as various amine derivatives, carboxylic acid derivatives, cyanohydrin derivatives and charged metal complexes by 1H NMR spectroscopy.

Description

[0001] Cross References to Related Applications [0002] This application claims priority under 35 U.S.C. §119 to Korean Patent Application No. 2015-0116903 filed with the Korean Intellectual Property Office on Aug. 19, 2015, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The following disclosure relates to novel ligands, chiral metal complexes containing them, and the use of said chiral metal complexes for 1 Use of H NMR spectroscopy to analyze the chirality of charged compounds. The chiral metal complexes of the present invention can be used as chiral solvating agents to pass 1 H NMR spectroscopy conveniently analyzes the optical purity of charged compounds such as various amine derivatives, carboxylic acid derivatives, cyanohydrin derivatives, and charged metal complexes. Background technique [0004] Many compounds exhibiting physiological activity are chiral and thus optically active. It is well known in the art t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/50G01N24/08
CPCG01N24/08C07B2200/07C07C215/50C07C2601/14C07F5/003C07F5/069C07F7/28
Inventor 金炫佑徐民燮
Owner KOREA ADVANCED INST OF SCI & TECH