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Synthesis of optical active cyanhydrin compound by enzyme chemical process

A compound, cyanohydrin technology, applied in the field of enzymatic chemical synthesis, can solve problems such as waste

Inactive Publication Date: 2006-03-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] As mentioned above, because the synthetic route of thiamphenicol and fluthiamphenicol involves the resolution of racemic compounds, only half of the intermediates can be used to synthesize the target compound of the desired configuration, resulting in a lot of waste

Method used

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  • Synthesis of optical active cyanhydrin compound by enzyme chemical process
  • Synthesis of optical active cyanhydrin compound by enzyme chemical process
  • Synthesis of optical active cyanhydrin compound by enzyme chemical process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1) Preparation of badam degreasing powder

[0046] Grind 50g of Badamia kernels in a tissue grinder, degrease with conventional organic solvents, such as 100mL of ethyl acetate, acetone or isopropyl ether, stir for 15 minutes to one hour, filter, and repeat washing 2 to 4 times to obtain The delipase powder is hydroxycyanolyase and stored in the refrigerator for later use.

[0047] After reacting sodium cyanide and glacial acetic acid, solvent extraction is used to obtain an organic solvent solution containing hydrocyanic acid, which is dried over anhydrous sodium sulfate and used; or directly adding hydrocyanic acid to an organic solvent containing 0-1% by weight of water.

Embodiment 2

[0049] 2) Synthesis of compound 2

[0050]

[0051] Add 400mg of compound 1, 0.15g of almond degreasing powder, 5ml of 1.5eq.HCN in isopropyl ether to a 25ml egg-shaped bottle, and react at 20°C for 24 hours. Filter, wash the enzyme source powder with ethyl acetate, and combine the organic phases. Organic phase with saturated FeCl 3 Aqueous wash to FeCl 3 The solution does not change color, Na 2 SO 4 dry. Colorless crystal product, yield 90%.

[0052] [α] D 20 +50.4(c0.83, CHCl 3 ), e.e.=96%;

[0053] 1 HNMR (CDCl 3 , 300MHz): δ, 2.50(s, 3H, CH 3 ), 3.00 (br, s, 1H, OH), 5.49 (s, 1H, CH), 7.29, 7.43 (AB, J 8.5Hz, 4H) ppm;

[0054] EI-MS: m / z (rel.intensty%): 181 (M + , 2, 5), 179 (M + , 79), 162 (M + -OH, 39), 153 (M + -CN, 55), 152 (M + -HCN, 100), 151 (M + -HCN-H, 88), 132(29), 123(16), 109(20), 105(17), 91(7), 77(17);

[0055] EA: Calculation: C: 60.31%, H: 5.06%, N: 7.82%

[0056] Found values: C: 60.40%, H: 5.06%, N: 7.73%

Embodiment 3

[0058] 3) Synthesis of compound 3

[0059]

[0060] Add compound 2 (0.9g), 2-Methoxypropene (20ml), CH to 250ml egg-shaped bottle 2 Cl 2 (150ml), POCl 3 (20 mg), stirred overnight at room temperature. Join Et 3 N 3mL, stirred for 30min, stopped. The organic phase was washed with saturated brine (50ml×3), anhydrous Na 2 SO 4 dry. Flash column chromatography (EA / PE=1 / 10) gave 1.09 g of a yellow solid with a yield of 96%. Recrystallization gave 0.92 g of colorless crystals with a yield of 77%.

[0061] 1 HNMR (CDCl 3 , 300MHz): δ, 1.4(s, 3H, CH 3 ), 1.58 (s, 3H, CH 3 ), 2.50(s, 3H, SCH 3 ), 3.2(s, 3H, OCH 3 ), 5.42 (s, 1H, CH), 7.25-7.41 (m, 4H, Hz, Ar-H) ppm, EI-MS: m / z (rel.intensity%): 251 (M + , 1.63), 219 (M + -H-OCH, 2.01), 179 (100.00), 162 (76.27), 151 (21.93), 132 (82.14), 109 (22.98), 105 (28.48), 86 (49.45), 45 (27.76);

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Abstract

This method discloses a zymochemistry method to synthesize optically active cyanohydrin compounds. By using hydroxyl-cyano lyase HNL---contained in almond, loquat seed, apple seed and Badawood seed to conduct catalytic reaction to obtain a new hydroxyl-cyano compound which can be used to synthesize various compounds such as thiamphenicol, florfenicol, etc..

Description

technical field [0001] The invention relates to an enzymatic chemical synthesis method, in particular to an enzymatic chemical synthesis of an optically active cyanohydrin compound. Background technique [0002] Thiamphenicol and fluthiamphenicol are broad-spectrum antibiotics of the chloramphenicol class. The antibacterial spectrum and antibacterial effect of thiamphenicol are similar to those of chloramphenicol. Since thiamphenicol does not combine with glucuronic acid in the liver, the antibacterial activity in vivo is relatively high. Florfenicol (florfenicol) 15, also known as florfenicol, is a new type of anti-gram-positive bacteria, negative bacteria and thiamphenicol florfenicol specially developed for the animal health market Florfenicol (Florfenicol) is a broad-spectrum antibacterial drug for animals. Its structure is similar to thiamphenicol, but its antibacterial activity, antibacterial spectrum and adverse reactions are obviously superior to thiamphenicol. Its ...

Claims

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Application Information

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IPC IPC(8): C07C323/62C07C317/38C12P13/00
Inventor 林国强卢文芽陈沛然
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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