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Preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid

A technology of dimethylvaleric acid and dimethylvaleric hydrochloride is applied in the preparation of carbamate derivatives, the preparation of organic compounds, the preparation of cyanide reactions, etc., and can solve the problem of low product yield and expensive enzyme catalysts and other problems, to achieve the effect of cheap and easy-to-obtain raw materials, low cost, and safe product yield

Active Publication Date: 2019-09-20
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has simple steps, the price of the enzyme catalyst used in the first step is relatively expensive and the product yield is low

Method used

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  • Preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid
  • Preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid
  • Preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid

Examples

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Comparison scheme
Effect test

Embodiment 1

[0031] A preparation method of N-Boc-(R)-2-amino-4,4-dimethylvaleric acid, comprising the following steps:

[0032] S1. Under nitrogen atmosphere, dissolve 3,3-dimethylbutyraldehyde (70g, 1.0eq) in 42mL of dichloromethane and add (R)-(+)-tert-butylsulfinamide (93.2g, 1.1eq ) and anhydrous copper sulfate (178.4g, 1.6eq), then stirred and reacted at 20°C for 12h, after the reaction was completed, filtered and concentrated to obtain (R,E)-N-(3,3-dimethyl Butylene)-2-methylpropane-2-sulfinamide, yield 76%;

[0033] S2. The (R,E)-N-(3,3-dimethylbutylene)-2-methylpropane-2-sulfinamide (107g, 1.0eq) was dissolved in n-hexane (749mL) and Add cesium fluoride (84g, 1.05eq), add trimethylsilyl cyanide (164.4g, 3.0eq) dropwise to the system under an inert atmosphere at -5°C, after the addition is complete, react at -5°C for 60h , add 40mL of saturated ammonium chloride to the system to quench, extract with ethyl acetate, dry the organic phase over anhydrous sodium sulfate, filter, conce...

Embodiment 2

[0037] A preparation method of N-Boc-(R)-2-amino-4,4-dimethylvaleric acid, comprising the following steps:

[0038] S1. Under a nitrogen atmosphere, dissolve 3,3-dimethylbutyraldehyde (70g, 1.0eq) in 50mL of dichloromethane and add (R)-(+)-tert-butylsulfinamide (93.2g, 1.0eq ) and anhydrous copper sulfate (33.45g, 0.3eq), then stirred and reacted at 20°C for 12h, after the reaction was completed, filtered and concentrated to obtain (R,E)-N-(3,3-dimethyl Butylene)-2-methylpropane-2-sulfinamide, yield 35%;

[0039]S2. The (R,E)-N-(3,3-dimethylbutylene)-2-methylpropane-2-sulfinamide (107g, 1.0eq) was dissolved in n-heptane (749mL) And add cesium fluoride (84g, 1.05eq), in an inert atmosphere and at -5°C, add trimethylsilyl cyanide (164.4g, 3.0eq) dropwise to the system, after the dropwise addition, react at 0°C for 72h , add 40mL of saturated ammonium chloride to the system to quench, extract with ethyl acetate, dry the organic phase over anhydrous sodium sulfate, filter, conce...

Embodiment 3

[0043] A preparation method of N-Boc-(R)-2-amino-4,4-dimethylvaleric acid, comprising the following steps:

[0044] S1. Under a nitrogen atmosphere, dissolve 3,3-dimethylbutyraldehyde (70g, 1.0eq) in 60mL of tetrahydrofuran and add (R)-(+)-tert-butylsulfinamide (101.7g, 1.2eq) and Anhydrous copper sulfate (278.75g, 2.5eq), then stirred and reacted at 20°C for 12h, after the reaction was completed, filtered and concentrated to obtain (R,E)-N-(3,3-dimethylbutylene )-2-methylpropane-2-sulfinamide, yield 60%;

[0045] S2. The (R,E)-N-(3,3-dimethylbutylene)-2-methylpropane-2-sulfinamide (107g, 1.0eq) was dissolved in n-heptane (749mL) And add cesium fluoride (84g, 1.05eq), in an inert atmosphere and at -5°C, add trimethylsilyl cyanide (164.4g, 3.0eq) dropwise to the system, after the dropwise addition, react at -5°C for 60h Finally, add 40 mL of saturated ammonium chloride to the system to quench, extract with ethyl acetate, dry the organic phase over anhydrous sodium sulfate, fi...

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Abstract

Belonging to the field of organic synthesis, the invention discloses a preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid. The preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid includes a synthetic route shown as the specification. The preparation method of N-Boc-(R)-2-amino-4, 4-dimethylvaleric acid provided by the invention has the advantages of cheap and easily available raw materials, low cost, convenient process operation, safety and high product yield, is suitable for industrial production, and has broad application prospects.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of N-Boc-(R)-2-amino-4,4-dimethylpentanoic acid. Background technique [0002] In 2008, Desantis, people such as Grace used 2-amino-4,4-dimethylvaleronitrile as starting material, and adopted the route shown in Figure (1) to obtain target product through two-step reaction (referring to " Efficient Synthesis of Novel NK1 Receptor Antagonists: Selective 1,4-Addition of Grignard Reagents to 6-Chloronicotinic Acid Derivatives”World Intellectual Property Organization, WO2008106662A22008-09-04). Although this method has fewer process steps, it is expensive, especially the first step is expensive by cyanohydrolase, and the reaction formula is as follows: [0003] [0004] In 2016, Zhao, Baoguo et al. used 4,4-dimethyl-2-oxopentanoic acid as the starting material, and used the route shown in Figure (2) to obtain the target product through a two-step r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/22
CPCC07C313/06C07C227/02C07C269/04C07C229/08C07C271/22
Inventor 李显军金海泉庄明晨罗建业郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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