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Synthetic method for beta-amino acids and beta-amino acids synthesized by adopting method

A synthesis method and amino acid technology, applied in the field of β-amino acids, can solve the problems of lack of structural diversity of β-amino acids, and achieve the effect of mild process conditions

Active Publication Date: 2018-03-13
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the β-amino acids synthesized by these methods are not substituted at the α and β positions at the same time, and the resulting β-amino acids lack structural diversity.

Method used

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  • Synthetic method for beta-amino acids and beta-amino acids synthesized by adopting method
  • Synthetic method for beta-amino acids and beta-amino acids synthesized by adopting method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of 3-((ethoxycarbonyl) amino) butanoic acid

[0028] 0.2mmol N-(2-(pyridin-2-yl)propan-2-yl)butanamide, 0.02mmol Pd(OAc) 2 , 0.4mmol diethyl azodicarboxylate and 1mL 2-methyl-2-butanol were added to the reaction flask, purged with oxygen, sealed and heated to 110°C for 24 hours, cooled to room temperature, distilled under reduced pressure and purified Compound (I) was obtained with a yield of 83%.

[0029] After dissolving 0.1 mmol of compound (I) and 0.2 mmol of methyl bromoacetate in acetonitrile, 0.25 mmol of cesium carbonate was added and reacted at 50°C for 1 h. After extraction, washing, and vacuum distillation to obtain a suspension, cesium carbonate and acetonitrile were used as solvents. After reflux reaction, colorless crystal compound (II) was obtained through extraction and vacuum distillation with a yield of 81%.

[0030] Add 0.05 mmol of compound (II) to hydrochloric acid at 140°C for 48 hours, cool and distill under reduced...

Embodiment 2

[0035] Embodiment 2: the preparation of 3-((ethoxycarbonyl) amino) phenylpropionic acid

[0036] 0.2mmol 3-phenyl-N-(2-(pyridin-2-yl)propan-2-yl)propanamide, 0.02mmol Pd(OAc) 2, 0.6mmol diethyl azodicarboxylate, 1mL 2-methyl-2-butanol were added to the reaction flask, purged with oxygen, sealed and heated to 100°C for 24 hours, cooled to room temperature, and the solvent was removed by distillation under reduced pressure. Compound (I) was obtained after purification with a yield of 87%.

[0037] After dissolving 0.1 mmol of compound (I) and 0.2 mmol of methyl bromoacetate in acetonitrile, 0.25 mmol of cesium carbonate was added and reacted at 50°C for 1 h. After extraction, washing, and vacuum distillation to obtain a suspension, cesium carbonate and acetonitrile were used as solvents, and after reflux reaction, colorless crystal compound (II) was obtained through extraction and vacuum distillation with a yield of 80%.

[0038] Add 0.05 mmol of compound (II) to hydrochloric ...

Embodiment 3

[0041] Embodiment 3: the preparation of 3-((ethoxycarbonyl) amino)-4-methylpentanoic acid

[0042] 0.2mmol 4-methyl-N-(2-(pyridin-2-yl)propan-2-yl)pentanamide, 0.04mmol Pd(OAc) 2 , 0.4mmol diethyl azodicarboxylate, and 1mL dichloroethane were added to the reaction flask, purged with oxygen, sealed and heated to 110°C for 24 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the compound was obtained after purification ( 1), yield is 66%.

[0043] After dissolving 0.1 mmol of compound (I) and 0.2 mmol of methyl bromoacetate in acetonitrile, 0.25 mmol of cesium carbonate was added and reacted at 60° C. for 2 h. After extraction, washing, and vacuum distillation to obtain a suspension, cesium carbonate and acetonitrile were used as solvents. After reflux reaction, colorless crystal compound (II) was obtained through extraction and vacuum distillation with a yield of 85%.

[0044] Add 0.05 mmol of compound (II) to hydrochloric aci...

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Abstract

The invention relates to a novel synthetic method for beta-amino acids and the beta-amino acids synthesized by adopting the method. The method comprises the following steps: an amide and an azo diacidester are taken as raw materials, an intermediate compound I is synthesized through direct carbon-hydrogen bond amination under the action of a catalyst, the intermediate compound I reacts with methyl bromoacetate to synthesize an intermediate compound II, an amide protecting group is removed under acidic conditions, and therefore the beta-amino acid is obtained; and the chemical structural formula of the beta-amino acid obtained by synthesis is shown in the description, wherein in a formula, R1 and R2 are separately one selected from the group consisting of hydrogen, alkyl, branched alkyl, cycloalkyl, aryl, aryl with various substituents, a heterocyclic group and a heterocyclic group with various substituents; and R3 is an ester group. Compared with the prior art, the method provided bythe invention synthesizes the intermediate compound I through the direct carbon-hydrogen bond amination process, so that substrates can be broadened in a wide range, the synthesized beta-amino acids with substituents in alpha and beta positions have structural diversity, and therefore the method provides a novel method for the industrialized production of the beta-amino acids with the substituentsin the alpha and beta positions.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a new synthesis method of β-amino acid and the β-amino acid synthesized by the method. Background technique [0002] In recent years, less β-amino acids in nature have received more and more attention. β-amino acid is the synthetic precursor of a large number of antibiotics with β-lactam structure, and some β-amino acid itself has biological activity, such as (S)-2-phenyl-3-aminopropionic acid is penicillin β-preferred Caine (Betacine) side chain, and its ethyl ester derivatives have neuroactivity. β-amino acids exist in some natural bioactive peptide chains, for example, (2S,3R)-2-hydroxy-3-amino-4-phenylbutyric acid exists in the famous immune response regulator Bestatin. Structurally functionalized β-amino acids are important building blocks of many bioactive molecules. The 13-position side chain of the well-known anticancer drug taxol (Taxol) is an α-hydro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/40C07D215/40C07C269/06C07C271/22C07C271/24
CPCC07C269/06C07D213/40C07D215/40C07C271/22C07C271/24Y02P20/55
Inventor 张书宇白贺元丁同梅
Owner SHANGHAI JIAO TONG UNIV
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