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Synthesis method of 2-([1, 1 '-biphenyl]-4-yl)-2-glycine compound
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A synthesis method and compound technology, applied in the field of organic compound synthesis, can solve the problems of long total reaction time, low safety, reduced safety and the like
Active Publication Date: 2020-10-30
马鞍山诺恩特医药科技有限公司
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[0006] In the above synthesis method, toxic and flammable substances-tert-butyl isocyanate are used in the raw materials, which has low safety
The second step reaction is still under high temperature conditions, the intermediate is reacted with concentrated hydrochloric acid, and the safety is further reduced
And the total reaction time is too long, the yield is not high
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Embodiment 1
[0062] Synthesis of 2-([1,1'-biphenyl]-4-yl)-2-glycine
[0063]
[0064] Under nitrogen protection conditions, phenylboronic acid (1.33g, 11mmol), 2-(tert-butoxycarbonyl-amino)-2-(4-bromophenyl)acetic acid (3.30g, 10mmol), 2 M K 2 CO 3 (3mL), 20mL of THF, after heating and stirring, add Pd(PPh 3 ) 4 (0.03g, 0.2%mmol), using a microwave-assisted instrument (80W) microwave-assisted for 3min, then stirring the reaction at 90°C for 8h, extracting with ethyl acetate, drying over anhydroussodiumsulfate, spinning off most of the solvent, and passing through a silica gelcolumn chromatography Purify by analysis and eluting with petroleumether / ethyl acetate (V / V=20:1) to obtain 2-([1,1'-biphenyl]-4-yl)-2-glycine protected by tert-butoxycarbonyl , then add 20% (V / V) TFA / CH 2 Cl 2 (30 mL), the reaction mixture was stirred at room temperature (25° C.) for 1 h, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous...
Embodiment 2
[0069] Synthesis of 2-amino-2-(3'-fluoro-[1,1'-biphenyl]-4-yl)acetic acid
[0070]
[0071] In this example, 3-fluorophenylboronic acid (11mmol) is used instead of phenylboronic acid, and the others are the same as in Example 1, the final product 2-amino-2-(3'-fluoro-[1,1'-biphenyl]-4-yl) Yield of acetic acid: 89%.
[0072] The NMR structure test results of the product are as follows:
[0073] 1 H NMR(400MHz,DMSO)δ8.55(m,2H),7.46(m,6H),7.29(m,1H),7.07(m,1H),5.20(m,1H).
[0076] Synthesis of 2-amino-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)acetic acid
[0077]
[0078] In this example, 2-fluorophenylboronic acid (11mmol) is used instead of phenylboronic acid, and the others are the same as in Example 1, the final product 2-amino-2-(2'-fluoro-[1,1'-biphenyl]-4-yl) Yield of acetic acid: 89%.
[0079] The NMR structure test results of the product are as follows:
[0080] 1 H NMR(400MHz,DMSO)δ8.75(m,2H),7.62(m,1H),7.52(dq,2H),7.44(m,2H),7.38(m,2H),7.18(m,1H) ,5.20(m,1H).
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Abstract
The invention relates to a synthesis method of a 2-([1, 1 '-biphenyl]-4-yl)-2-glycine compound. The method comprises the following steps: performing suzuki reaction on a compound as shown in a formulaI and a compound as shown in a formula II in the presence of alkali, a solvent and a catalyst under inertgas protection and microwave-assisted conditions to prepare an intermediate compound, and then deprotecting the intermediate compound to prepare a compound as shown in a formula III, wherein the structural formula of the compound shown in the formula I is shown in the specification, the structural formula of the compound shown in the formula II is shown in the specification, the structural formula of the compound shown in the formula III is shown in the specification, and in the formula Iand the formula III, R is one of H, alkyl, alkoxy, halogen and trifluoromethyl. The synthesis method is low in toxicity, high in safety coefficient, easy and convenient to operate, easy to control and efficient in reaction, and the yield reaches up to 81% or above. In the synthesis method, microwave assistance is added for a certain time in the suzuki reaction process, so that the reaction is promoted, the reaction efficiency is effectively improved, and the reaction time is shortened.
Description
technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to a method for synthesizing 2-([1,1'-biphenyl]-4-yl)-2-glycine compounds. Background technique [0002] 2-([1,1'-biphenyl]-4-yl)-2-glycine compounds with monosubstituted or unsubstituted benzene rings in amino acid derivatives are an important class of pharmaceutical intermediates and are used in the field of medicinal chemistry Very broad, such as intermediates for the synthesis of protease inhibitor compounds and their pharmaceutical compositions. [0003] However, at present, there is less research on the preparation method of this type of compound. In the published synthetic method about this type of compound, 4-biphenylcarbaldehyde is generally used as the starting material, such as the synthetic method disclosed in the patent WO2003010130, the route as follows: [0004] [0005] The synthesis steps are as follows: using 4-biphenylformaldehyde as the st...
Claims
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