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Linear polystyrene supported (4S)-5,5-disubstituted oxazolidin one and its preparation method and uses

A technology of dimethyl oxazolidinone and base oxazolidinone is applied in the field of on-line polystyrene support-5, which can solve the structural destruction of chiral auxiliary reagents, the side reaction of oxazolidinone ring opening, and the production of products. problems such as low yield, to achieve the effects of good yield, difficult ring opening, and simple post-reaction treatment

Inactive Publication Date: 2008-06-18
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The problem is that when there is no substituent on the oxazolidinone ring, the oxazolidinone is prone to ring-opening side reactions when the product is released from the chiral auxiliary reagent, resulting in low product yields, and the structure of the chiral auxiliary reagent is partially affected. destruction etc.
In order to overcome the above-mentioned deficiencies, the present invention adopts No. 5 of oxazolidinone that has two substituents 5,5-diphenyl and 5,5-dimethyl-substituted oxazolidinones to overcome the above-mentioned simple structure of the oxazolidinone The disadvantage of easy ring opening when oxazolidinone is released, and 5,5-disubstituted oxazolidinone is supported on a soluble polymer to prepare linear polystyrene-supported 5,5-disubstituted oxazolidinone oxazolidinone

Method used

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  • Linear polystyrene supported (4S)-5,5-disubstituted oxazolidin one and its preparation method and uses
  • Linear polystyrene supported (4S)-5,5-disubstituted oxazolidin one and its preparation method and uses
  • Linear polystyrene supported (4S)-5,5-disubstituted oxazolidin one and its preparation method and uses

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] SOCl 2 (12mL, 0.17mol) was added to methanol (120mL), the temperature was kept at -10°C for 20 minutes, L-tyrosine (25.0g, 0.14mol) was added, reacted at 20°C for 72h, methanol was removed, and the residue was dissolved in After heating with methanol, it was recrystallized with anhydrous ether, filtered, washed with ether, and dried in vacuo to give a white solid, L-tyrosine methyl ester hydrochloride (31.1 g, 96.2%). m.p.187-189°C (lit.190-191°C); [α] D 20 =+69.8(c 1.06, pyridine)[lit[α] D 20 =+70.9(c 1.1, pyridine)]; IR: 3350, 3213, 1743, 1596, 1515, 1445, 843cm -1 ; 1 HNMR: 7.06 (2H, d, ArH), 6.80 (2H, d, ArH), 4.28 (1H, m, CH), 3.74 (3H, s, CH 3 ), 3.16 (1H, m, CH 2 ), 3.08 (1H, m, CH 2 ); 13 CNMR: 170.3, 155.4, 131.0 (2C), 125.6, 116.1 (2C), 54.4, 53.7, 34.9.

Embodiment 2

[0038] SOCl 2(36mL, 0.51mol) was added to methanol (120mL), the temperature was kept at -10°C for 20 minutes, L-tyrosine (25.0g, 0.14mol) was added, reacted at 70°C for 12h, methanol was removed, and the residue was dissolved in After heating with methanol, it was recrystallized with anhydrous ether, filtered, washed with ether, and dried in vacuo to obtain a white solid, L-tyrosine methyl ester hydrochloride (29.4 g, 90%). m.p.187-189°C (lit.190-191°C); [α] D 20 =+69.8(c 1.06, pyridine)[lit.[α] D 20 =+70.9(c 1.1, pyridine)]; IR: 3350, 3213, 1743, 1596, 1515, 1445, 843cm -1 ; 1 HNMR: 7.06 (2H, d, ArH), 6.80 (2H, d, ArH), 4.28 (1H, m, CH), 3.74 (3H, s, CH 3 ), 3.16 (1H, m, CH 2 ), 3.08 (1H, m, CH 2 ); 13 CNMR: 170.3, 155.4, 131.0 (2C), 125.6, 116.1 (2C), 54.4, 53.7, 34.9.

[0039]

Embodiment 3

[0041] Dissolve L-tyrosine methyl ester hydrochloride (10g, 0.043mol) in 100mL of a mixed solution of 1,4-dioxane and water (1:1, v / v), and add triethyl ether at 0°C Amine (10mL, 0.07mol), di-tert-butyl dicarbonate (7.3g, 0.042mol), stirred at 20°C for 48h, diluted with water and ethyl acetate, separated the organic phase, and extracted the aqueous phase with ethyl acetate (20mL×3 ), after the organic phases were combined, they were dried over anhydrous magnesium sulfate. Colorless crystals obtained after removal of ethyl acetate were (2S)-2-(N-tert-butoxycarbonyl)amino-3-(4'-hydroxyphenyl)-propionic acid methyl ester (10.3 g, 81%). m.p.104-105°C, [α] D 20 =+20.4 (c 0.72, THF); IR: 3365, 2978, 1740, 1689, 1516, 828; 1 HNMR: 6.96 (2H, d, ArH), 6.72 (2H, d, ArH), 5.03 (1H, m, OH), 4.54 (1H, m, CH), 3.71 (3H, s, OCH 3 ), 3.01 (1H, m, CH 2 ), 2.98 (1H, m, CH 2 ), 1.42 (9H, s, CH 3 ); 13 CNMR: 173.1, 155.8, 155.6, 130.8 (2C), 127.9, 115.9 (2C), 80.7, 55.0, 52.7, 38.0, 28.7 ...

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Abstract

The invention relates the direction of twist polyphenylacetylene (4S) - 5, 5- dissubstituent oxazolidinone 1 and 2. The invention comprises the following steps: using L- tyrosine, carrying out esterification, amination and Grignard addition, polymerizing, and getting compound. The invention has the advantages of low cost, simple final treatment and good productivity.

Description

technical field [0001] The invention relates to a linear polystyrene-supported (4S)-5,5-disubstituted oxazolidinone, a preparation method and application thereof. Background technique [0002] Since Merrifield first used insoluble polymers to support the synthesis of peptides in 1963, especially in recent years with the need for a large number of screening drugs, solid-phase organic synthesis has been greatly developed. Compared with the classic liquid-phase synthesis, solid-phase organic synthesis has many advantages, showing strong vitality and attractiveness, which are shown in: (1) it is convenient for rapid separation and purification during the reaction process, and it simplifies the separation and purification of the target product; (2) it can Increase the reaction yield by increasing the amount of liquid phase reactants, and the excess reactants in the liquid phase can be removed by washing after the reaction is completed; (3) it is convenient to realize programmed a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F212/08C08F4/04C08F212/14
Inventor 万亚东陈祖兴杨桂春卢翠芬
Owner HUBEI UNIV