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Acid absorbing agent for preparing cinchona alkaloids ligand

A technology for cinchona alkaloids and ligands, which is applied in the field of acid binding agents, can solve the problems of difficulty in accurate quantification, danger, easy combustion, etc., and achieves the effects of avoiding the column chromatography process, easy operation and safe use.

Inactive Publication Date: 2007-04-18
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although NaH is used as an acid-binding agent under mild reaction conditions, it is well known that NaH is easily hydrolyzed and burned in the air. Commercial NaH is wrapped and protected with esters. When using it, wash off the coating with anhydrous ether, and then weigh it accurately. quantitative difficulty
At the same time, it is extremely flammable when operating in areas with high humidity
The use of ether is also dangerous in industrial production

Method used

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  • Acid absorbing agent for preparing cinchona alkaloids ligand
  • Acid absorbing agent for preparing cinchona alkaloids ligand
  • Acid absorbing agent for preparing cinchona alkaloids ligand

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of ligand 1

[0027] Add 0.295g (0.0015mol) 1,4-dichloro-2,3-naphthalene, 0.975g (0.003mol) dihydroquinine, 0.63g (0.015mol) CaH into a 100mL three-necked flask 2 , 4.5mL DMF, N 2 Protected and reacted at 90°C. The reaction solution was a pale yellow turbid solution. TLC monitored the reaction process until the raw materials disappeared. The total reaction time was 1 h. Add 10mL ethyl acetate and 5mL water and stir, separate the water layer, extract with ethyl acetate (15mL×3), combine the organic phases, anhydrous MgSO 4 dry. When about 3 mL of liquid was left after filtration and concentration under reduced pressure, white needle-like crystals were deposited, drained, and washed with a little anhydrous ether to obtain white crystals. The yield was 95%. m.p.133~135℃. 1 H NMR(CDCl 3 , Internal standard TMS): δ8.65(d, J=4.6Hz, 2H), 8.33(m, 2H), 7.98(d, J=9.2Hz, 2H), 7.96(m, 2H), 7.56(d, 2H), 7.44(d, J=4.7Hz, 2H), 7.36(d, 1H), 7.35(d, 1H), 7.01(d, 2H), 3....

Embodiment 2

[0028] Example 2: Synthesis of ligand 2

[0029] Add 0.295g (0.0015mol) 1,4-dichloro-2,3-naphthalene, 0.975g (0.003mol) dihydroquinidine, and 0.63g (0.015mol) CaH in a 100mL three-necked flask 2 , 4.5mL N, N-dimethylformamide (DMF), N 2 Protected and reacted at 90°C. The reaction liquid was a pale yellow turbid solution. The reaction process was monitored by TLC until the raw materials disappeared. The total reaction time was 5 hours. Add 10mL ethyl acetate and 5mL water and stir, separate the water layer, extract with ethyl acetate (15mL×3), combine the organic phases, anhydrous MgSO 4 dry. When about 3 mL of liquid was left after filtration and concentration under reduced pressure, white needle-like crystals were deposited, drained, and washed with a little anhydrous ether to obtain white crystals. The yield was 78%. m.p.176~178℃. 1 H NMR(CDCl 3 , Internal standard TMS): δ8.65(d, J=5.3Hz, 2H), 8.33(m, 2H), 7.98(d, J=9.2Hz, 2H), 7.94(m, 2H), 7.58(d, 2H), 7.43(d, J=5.2Hz, 2H), 7.3...

Embodiment 3

[0030] Example 3: Synthesis of Ligand 3

[0031] Add 0.295g (0.0015mol) 1,4-dichloro-2,3-phthalazinone, 0.97g (0.003mol) quinine, 0.63g (0.015mol) CaH into a 100mL three-necked flask 2 , 4.5mL DMF, N 2 Protected and reacted at 90°C. The reaction liquid was a pale yellow turbid solution. The reaction process was monitored by TLC until the raw materials disappeared. The total reaction time was 6 hours. Add 10mL ethyl acetate and 5mL water and stir, separate the water layer, extract with ethyl acetate (15mL×3), combine the organic phases, anhydrous MgSO 4 dry. When about 3 mL of liquid was left after filtration and concentration under reduced pressure, white needle-like crystals were deposited, drained, and washed with a little anhydrous ether to obtain white crystals. The yield was 95%. m.p.160~161℃. 1 H NMR(CDCl 3, Internal standard TMS): δ8.65(d, J=5.3Hz, 2H, Ar-H), 8.33(m, 2H, Ar-H), 7.98(d, J=9.2Hz, 2H, Ar-H) , 7.96 (m, 2H, Ar-H), 7.58 (s, 2H, Ar-H), 7.44 (d, J=5.2 Hz, 2H, Ar-H)...

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Abstract

The invention discloses the use of CaH2 in synthesizing cinchona alkaloid ligand, wherein the ligand has a structure disclosed in the specification. CaH2 can be used as the acid binder in synthesizing cinchona alkaloid ligand. monosubstituted product or disubstituted product including hydroquinine, Quinidine, Dihydroquinidine and their derivatives.

Description

Technical field [0001] The invention relates to an acid binding agent in the synthesis process of preparing chiral cinchona alkaloid ligands. Such ligands can be effectively used in asymmetric dihydroxylation and aminohydroxylation reactions of olefins. Background technique [0002] Chirality is one of the characteristics of nature and the basis of all life. The phenomenon of life depends on the existence and recognition of chirality. All animals, plants, and the human body have precise chiral recognition capabilities for drugs. The configuration of chiral drugs is different, and their physiological activity and toxicity are also different. L-dopa is a good medicine to treat Parkinson's disease, but D-dopa has serious side effects. The efficacy of (S)-naproxen is 35 times that of (R)-isomer. Therefore, how to obtain chiral compounds has become a severe challenge for chemists. Although optically pure compounds can be obtained through classic racemate resolution and chiral source s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D453/04C07D519/00
Inventor 孙晓莉张生勇南鹏娟
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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