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L-prolinamide derivative, preparation method and application of same

A technology of prolineamide and derivatives, applied in the field of chemistry, can solve problems such as cost increase, and achieve the effects of easy operation and high selectivity

Inactive Publication Date: 2010-11-24
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these reactions require high doses of catalysts to complete, making industrial applications costly

Method used

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  • L-prolinamide derivative, preparation method and application of same
  • L-prolinamide derivative, preparation method and application of same
  • L-prolinamide derivative, preparation method and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation of embodiment 1, L-prolineamide derivative b

[0025]

[0026] A. The preparation of intermediate g: under argon protection, temperature 0 ℃, add N-Boc-L-pro (4.7g, 22mmol) and triethylamine (2.3g, 22mmol) to anhydrous dichloromethane solution (80mL) was slowly added dropwise ethyl chloroformate (2.6g, 24mmol), after the addition was completed, stirred at 0°C for 30 minutes, then slowly added dropwise anhydrous dichloromethane solution (15mL) of compound f (4.9g, 20mmol), Add and react at room temperature for 4 hours; after the reaction is completed, the reaction mixture is successively washed with potassium bisulfate solution, saturated sodium bicarbonate solution, and saturated sodium chloride solution with a concentration of 1mol / L, dried over anhydrous sodium sulfate, and then distilled under reduced pressure The solvent was removed to obtain a crude product, which was purified by flash column chromatography to obtain 8.6 g of the target intermedi...

Embodiment 2

[0028] The preparation of embodiment 2, L-proline amide derivative c

[0029]

[0030] A. Preparation of intermediate i: prepared according to the method described in Example 1, except that "compound f (4.9g, 20mmol) in anhydrous dichloromethane solution (15mL)" was replaced by "compound h (2.9g, 10mmol) Anhydrous dichloromethane solution (15mL)" to obtain 4.7g of the target intermediate i (white solid), with a yield of 95%. mp 209-210°C; [α] 20 D =-21.50 (c=0.1, CH 2 Cl 2 ); 1 HNMR (300MHz, CDCl 3 )(ppm)=1.63(s, 9H), 1.76(s, 2H), 1.87-2.07(m, 4H), 3.38(s, 3H), 3.69-3.73(m, 2H), 4.16(s, 2H) , 4.38-4.45(m, 1H), 5.12-5.35(d, 1H), 6.38-6.74(d, 1H), 7.38-7.43(m, 2H), 7.57-7.59(m, 2H), 7.75-7.78( d, 2H); 13 CNMR (75MHz, CDCl 3 ) (ppm) = 24.7, 25.7, 28.3, 30.7, 33.5, 46.7, 48.5, 80.6, 122.2, 123.4, 126.6, 127.2, 128.1, 131.1, 131.2, 131.3, 133.4, 133.8, 164.1, 165.5, HRMS (ESI (172.0; ): (C 28 h 33 o 5 N 3 Na) + The calculated value of is 514.2312 and the measured ...

Embodiment 3

[0032] The preparation of embodiment 3, L-proline amide derivative d

[0033]

[0034] A. Preparation of intermediate g: prepared according to the method described in Example 1.

[0035] B. Preparation of L-prolinamide derivative d: Intermediate g (440mg, 1mmol) and hydrazine hydrate (0.12mL) were refluxed in ethanol (5mL) for 2 hours; ) was diluted to precipitate phthalic hydrazide, filtered, and the filtrate was distilled off under reduced pressure to obtain a crude product. The crude product was dissolved with dilute hydrochloric acid (2mL), filtered, and the filtrate was adjusted to pH 7 with saturated sodium bicarbonate solution. , extracted 3 times with dichloromethane (each 20mL), combined the dichloromethane extracts, washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then distilled off the solvent under reduced pressure to obtain the target product d (white solid ) 0.265g, yield 85%. 1 HNMR (300MHz, CDCl 3 )(ppm)=1.10-1.3...

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Abstract

The invention relates to L-prolinamide derivative of the general formula I, a preparation method and application of the same, belonging to the chemical field. The preparation method comprises following steps of: coupling N-Boc-L-Pro to mono terminal protecting (R,R)-1,2-cyclohexanediamine of the general formula II to obtain intermediate of the general formula III, processing the obtained intermediate by using trifluoroacetic acid to remove a Boc protecting group or by using hydrazine hydrate and ethanol to remove a mono terminal protecting group to obtain the L-prolinamide derivative of the general formula I. The L-prolinamide derivative can be used as the catalyst of the intermolecular asymmetric direct Aldol reaction, has the advantages of high efficiency, high selectivity, easy operation, recycling and the like and is suitable for large-scale industrial application. The invention further discloses a method for catalyzing the intermolecular asymmetric direct Aldol reaction by using the L-prolinamide derivative.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to L-prolineamide derivatives and their preparation methods and applications. Background technique [0002] Asymmetric synthesis is one of the most active fields of chemical development today, and plays a very important role in the development of chiral drugs, materials and spices and other chemicals. Traditional asymmetric synthesis mainly uses biocatalysts and metal catalysts. In recent years, more and more attention has been paid to metal-free organic small molecule catalysts, which mainly have the following advantages: (1) no metal is required to initiate, which can avoid environmental pollution by toxic metals; (2) low price, easy to modify and preparation; (3) easy to operate, can catalyze the reaction in wet solvent or air, without harsh anhydrous and oxygen-free conditions; (4) easy to separate and recover from the product. [0003] The aldol reaction (Aldol reaction) is one of th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/16C07D403/12C07D401/12B01J31/02B01J31/04C07B53/00C07C205/45C07C201/12C07C49/747C07C49/753C07C45/73C07C255/56C07C253/30C07D307/46C07D333/22
CPCY02P20/55
Inventor 官智何延红杨阳
Owner SOUTHWEST UNIVERSITY
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