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A class of chiral beta-hydroxyamide compounds, preparation method and applications thereof,

A technology for hydroxyamides and compounds is applied in the field of chiral beta-hydroxyamide compounds and their preparation, and can solve the problems of low yield, complicated preparation of raw materials, low stereoselectivity and the like

Active Publication Date: 2020-03-03
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the synthesis of chiral β-hydroxylamide compounds, the existing synthetic methods still have the disadvantages of low yield, complicated preparation of raw materials, and low stereoselectivity, so a new synthetic method for chiral β-hydroxylamide compounds is developed is very necessary

Method used

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  • A class of chiral beta-hydroxyamide compounds, preparation method and applications thereof,
  • A class of chiral beta-hydroxyamide compounds, preparation method and applications thereof,
  • A class of chiral beta-hydroxyamide compounds, preparation method and applications thereof,

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1, chiral amide carboxylic acid compound Ia shown in preparation formula I-1 (R 1 is -COOH, n is 3)

[0073] according to figure 1 Shown reaction equation prepares chiral amide carboxylic acid compound Ia (R 1 is -COOH, n is 3),

[0074] The specific implementation method is:

[0075] Get the Rhodococcus erythropolis AJ270 thalline of 2 grams wet weight (bacterial activity is: 1 * 10 7 -1×10 9 CFU / g), thawed at 30°C for 30 minutes, washed the bacteria with a buffer solution of dipotassium hydrogen phosphate and potassium dihydrogen phosphate (0.1M, pH 7.0, 50ml) into an Erlenmeyer flat-bottomed flask with screw top, dispersed Shake well and place in a shaker for 30 minutes at 30°C for activation, then add 1 mmol (186 mg) of the compound represented by formula IIa at one time, put it in a shaker at 30°C and 200 rpm for catalytic hydrolysis. Whole reaction TLC monitors, stops reaction after reacting 12h, and gained reaction liquid is removed thalline by o...

Embodiment 2

[0085] Embodiment 2, chiral amide carboxylate compound Ib shown in preparation formula I-2 (R 1 is-COOBn, n is 3)

[0086] according to image 3 Shown reaction equation prepares chiral amide carboxylic acid compound I b (R 1 is -COOBn, n is 3),

[0087] The specific implementation method is:

[0088] Take 2 grams of Rhodococcus erythropolis AJ270 bacteria in wet weight, thaw at 30°C for 30 minutes, wash the bacteria into the threaded port with a buffer solution of dipotassium hydrogen phosphate and potassium dihydrogen phosphate (0.1M, pH 7.0, 50ml) In a Erlenmeyer flat-bottomed flask, disperse and shake well, put it in a shaker for activation at 30°C for 30 minutes, then add 1 mmol (186 mg) of the compound represented by formula IIa at one time, put it in a shaker at 30°C, and carry out at 200rpm Catalyzes the hydrolysis reaction. The entire reaction was monitored by TLC, and the reaction was stopped after 12 hours of reaction. The resulting reaction solution was filtere...

Embodiment 3

[0096] Embodiment 3, the chiral amide carboxylate compound Ic shown in preparation formula I-2 (R 1 for-COOCH 2 C 6 h 4 Br, n is 3)

[0097] according to Figure 4 Shown reaction equation prepares chiral amide carboxylic acid compound Ic (R 1 for-COOCH 2 C 6 h 4 Br, n is 3),

[0098] The specific implementation method is: take 2 grams of Rhodococcus erythropolis AJ270 thallus with wet weight, thaw it for 30 minutes at 30°C, and thaw the bacteria with a buffer solution of dipotassium hydrogen phosphate and potassium dihydrogen phosphate (0.1M, pH7.0, 50ml). Wash the body into an Erlenmeyer flat-bottomed flask with a threaded opening, disperse and shake it evenly, and put it in a shaker for 30 minutes at 30°C, then add 1 mmol (186 mg) of the compound shown in Formula IIa at one time, and put it in a shaker for 30 minutes. The catalytic hydrolysis reaction is carried out at 200 rpm. The entire reaction was monitored by TLC, and the reaction was stopped after 12 hours of...

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Abstract

The invention discloses a chiral beta-hydroxyamide compound and a preparation method thereof, wherein the compound is represented by a formula I. According to the invention, the raw material for preparing a non-natural chiral amino acid compound is obtained by carrying out catalytic hydrolysis on a prochiral diamide compound II with different substituents by using a Rhodococcus erythropolis AJ270microbial system, wherein the use amount of the Rhodococcus erythropolis can be adjusted according to the use amount of a substrate, the reaction solvent is a common buffer solution with the pH valueof 6.0-8.0, the temperature is 20-37 DEG C, the reaction time is 3-120 h, and the Rhodococcus erythropolis microbial catalytic system can be cultured through fermentation and conveniently stored; andwith the application of the biotransformation to prepare chiral monoamide carboxylic acid and dicarboxylic acid, the characteristics of simplicity and convenience in operation, high reaction efficiency, mild reaction conditions, high enantioselectivity, easiness in product separation and high product purity are achieved, and the application prospect is god.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a chiral β-hydroxyamide compound, a preparation method and application thereof. Background technique [0002] Chiral β-hydroxyamide compounds widely exist in the structures of biologically active drugs and natural products. For example, the anticancer drug Vincaleukoblastine and the antibacterial drug Pneumocandin A0. For the synthesis of chiral β-hydroxyamide compounds, the existing synthetic methods still have the disadvantages of low yield, complicated preparation of raw materials, and low stereoselectivity. Therefore, a new synthesis method for chiral β-hydroxyamide compounds is developed. is very necessary. [0003] Biocatalysis is by far the most efficient, highly selective and environmentally friendly process, and the use of biocatalysis to synthesize some high value-added chemicals, especially chiral chemicals, has important application prospects and signifi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/40C07C231/12C07C231/02C07C67/343C07C69/757C12P13/02A61P35/00C07C235/06
CPCA61P35/00C07B2200/07C07C67/343C07C69/757C07C231/02C07C231/12C07C235/06C07C235/40C12P13/02C07C2601/14
Inventor 胡慧娟敖宇飞王德先王其强
Owner INST OF CHEM CHINESE ACAD OF SCI
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