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Method for producing amino acid amide derivative having fluorine-containing carbamate group, production intermediate thereof, and method for producing ethylene diamine derivative

A manufacturing method, arylalkyl technology, applied to the preparation of carbamic acid derivatives, preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of expensive use, low yield, long time, etc.

Active Publication Date: 2013-05-29
MITSUI CHEM AGRO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the above methods use amino acid amides, which are expensive and not readily available in large quantities, and thus are economically unfavorable
In addition, the reaction to synthesize amino acid amides from amino acids usually takes a long time and is low yield

Method used

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  • Method for producing amino acid amide derivative having fluorine-containing carbamate group, production intermediate thereof, and method for producing ethylene diamine derivative
  • Method for producing amino acid amide derivative having fluorine-containing carbamate group, production intermediate thereof, and method for producing ethylene diamine derivative
  • Method for producing amino acid amide derivative having fluorine-containing carbamate group, production intermediate thereof, and method for producing ethylene diamine derivative

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Experimental program
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preparation example Construction

[0139] The production method of the compound represented by the general formula (3) is explained below.

[0140] The compound represented by the general formula (3) is obtained by reacting an amino acid with a fluorine-substituted alkyl chloroformate in the presence of water, as in Non-Patent Document 1. As the alkyl chloroformate substituted with fluorine, commercially available products or those synthesized by the method of Patent Document 2 or the like can be used.

[0141] As the preparation method of the compound represented by the general formula (3), by dissolving the amino acid in water, while keeping the pH of the reaction solution at 11 to 13, dropwise adding an alkyl chloroformate substituted by fluorine to allow the reaction to be carried out efficiently. to get.

[0142] As an example of the compound represented by general formula (3), the compound represented by general formula (3') can be used.

[0143]

[0144] (where, R 1 Represents an alkyl group with 1...

Embodiment 1

[0217](Example 1) Synthesis of N-(2,2,2-trifluoroethoxycarbonyl)-L-alanine

[0218]

[0219] 50.8 g of L-alanine and 100 g of water were charged into a 1000 mL four-necked flask equipped with a stirring device, cooled to 5° C., and adjusted to pH 12 with 32% by weight NaOH. While keeping the pH at 12±0.5 and below 10°C, add dropwise a mixed solution of 93.5 g of chloroformic acid 2,2,2-trifluoroethyl ester and 200 g of toluene, and then proceed for 1 hour while maintaining the pH at pH 12±0.5 Stir. Hydrochloric acid was added dropwise to adjust the pH to 1.5, and then the temperature was raised to 60° C. for liquid separation. The organic layer was concentrated under reduced pressure to obtain a white solid compound which was the title compound.

[0220] Yield 24.5g (yield 20%)

[0221] 1 H NMR (CDCl3) δ1.51 (3H, d, J = 7.32Hz), 4.40-4.53 (3H, m), 5.45 (1H, d, J = 8.79Hz).

[0222] LC-MS M+1(216)

Embodiment 2

[0223] (Example 2) Synthesis of N-(2,2,2-trifluoroethoxycarbonyl)-L-alanyl chloride (alaninochloride)

[0224]

[0225] In a 100mL four-necked flask with a stirring device, put 10g of dichloromethane, 1.0g of N-(2,2,2-trifluoroethoxycarbonyl)-L-alanine, N,N-dimethyl 1 drop of methyl formamide (hereinafter DMF), cooled to 5°C, 0.90 g of oxalyl chloride was added dropwise, and stirred for further 2 hours while maintaining the temperature at 5°C. After concentrating under reduced pressure, 10 g of dichloromethane was added to the obtained oily residue, stirred for 10 minutes, and then concentrated under reduced pressure to obtain an oily substance. The obtained compound as an oily substance was the title compound.

[0226] Yield 1.08g (yield 99.5%)

[0227] 1 H NMR (CDCl3) δ1.59 (3H, d, J=7.32Hz), 4.40-4.65 (3H, m), 5.48 (1H, br).

[0228] IR (ATR method) cm -1 3330, 1779, 1716, 1525, 1454, 1413, 1383, 1285, 1243, 1162, 1121, 1088, 1049, 985, 897, 839, 774, 739, 637, 554,...

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Abstract

Disclosed is a method for producing a compound represented by general formula (2) by causing a compound represented by general formula (1) to react with ammonia.

Description

technical field [0001] The present invention relates to a method for producing an amino acid amide derivative having a fluorine-containing carbamate group, an intermediate for its production, and a method for producing an ethylenediamine derivative. Background technique [0002] As shown in Patent Document 1, it is known that an amino acid amide derivative having a fluorine-containing carbamate group is useful as an intermediate of a fungicide. When producing such a compound group, it is important to efficiently prepare it from readily available amino acids. [0003] Regarding the amino acid amide derivative having a fluorine-containing carbamate group, if the conventional production technology is cited, a method of reacting an amino acid amide with a fluorine-containing alkyl chloroformate as shown in Patent Document 1 . Here, the fluorine-containing alkyl chloroformate can be produced by a method of reacting a fluorine-containing alcohol with carbonyl chloride as disclos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/22C07D207/16
CPCC07C271/22C07D207/16C07C269/06
Inventor 梅谷豪毅河野敏之龟川尚登
Owner MITSUI CHEM AGRO INC
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