Preparation method of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-methyl propionate and intermediate of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-methyl propionate

A technology of methoxycarbonylmethyl and tert-butoxycarbonyl, applied in the field of compound synthesis, can solve the problem of low yield and achieve the effect of improving product yield

Pending Publication Date: 2022-04-22
郑州猫眼农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the prior art, Unexpected Insertion of Nitrogen into aC-C Bond: Access to 2,3-Disstituted Quinazolinone Scaffolds (Liu, Hui-Li et al, Organic Letters, 23(12), 4579-4583; 2021) discloses glycine methyl Ester hydrochloride reacts with methyl acrylate to obtain 3-(methoxycarbonylmethyl-amino)-methyl propionate, the catalyst used is sodium hydroxide, the solvent is methanol, and the yield is 69%, which is relatively low

Method used

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  • Preparation method of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-methyl propionate and intermediate of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-methyl propionate

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Embodiment 1

[0019] The preparation method of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester of the present embodiment comprises the following steps: take a dry 250mL three-necked bottle, and add 12.6g of glycine methyl ester salt acid salt, add 252mL of methanol, start stirring, add 2.6g of TMSOK and 15.2g of DBU, then slowly add 25.8g of methyl acrylate dropwise, after the addition, it rises to 40°C, and after 1h of reaction, it drops to 25°C ℃, add 21.8g of Boc anhydride, stir at 25℃ for 2h, stop the reaction, concentrate to dryness, add 100mL of water, dissolve and extract three times with dichloromethane, combine the organic phase, wash the organic phase with saturated brine once, and then Dry over anhydrous sodium sulfate and concentrate to dryness to obtain 26.4 g of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester, 3-(tert-butoxycarbonyl-methoxy The yield of carbonylmethyl-amino)-propionic acid methyl ester is 96%, and...

Embodiment 2

[0023] The preparation method of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester of the present embodiment comprises the following steps: take a dry 250mL three-necked bottle, and add 12.6g of glycine methyl ester salt salt, add 252mL of methanol, start stirring, place the reaction bottle in an ice-water bath, add 2.6g of TMSOK and 15.2g of DBU, then slowly add 25.8g of methyl acrylate dropwise, after the addition, it rises to 40 ℃, continue stirring for 3h, add 21.8g of Boc anhydride, then rise to 25°C, stir at this temperature for 2h, stop the reaction, concentrate to dryness, add 100mL of water, dissolve and extract three times with dichloromethane, and combine the organic phases , the organic phase was washed once with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain 21.2 g of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester, 3 Yield of -(tert-butoxycarbonyl-methoxycar...

Embodiment 3

[0025] The preparation method of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester of the present embodiment comprises the following steps: take a dry 250mL three-necked bottle, and add 12.6g of glycine methyl ester salt Add 252mL of methanol, start stirring, add 2.6g of TMSOK and 15.2g of DBU, then slowly add 25.8g of methyl acrylate dropwise, after the addition, raise the reaction to 65°C, continue stirring for 1h, Add 21.8g of Boc anhydride, then raise it to 25°C, stir at this temperature for 2h, stop the reaction, concentrate to dryness, add 100mL of water, dissolve and extract three times with dichloromethane, combine the organic phase, and use saturated brine for the organic phase Washed once, dried with anhydrous sodium sulfate, and concentrated to dryness to obtain 23.5 g of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester, 3-(tert-butoxycarbonyl -Methoxycarbonylmethyl-amino)-propionic acid methyl ester yield...

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Abstract

The invention relates to a preparation method of 3-(tert-butoxycarbonyl-methoxycarbonyl methyl-amino)-methyl propionate and an intermediate thereof, and the preparation method of the 3-(methoxycarbonyl-methyl-amino)-methyl propionate comprises the following steps: dissolving glycine methyl ester hydrochloride in a solvent, adding potassium trimethylsilanolate, stirring, reacting, filtering, washing, and drying to obtain the 3-(tert-butoxycarbonyl-methoxycarbonyl methyl-amino)-methyl propionate. And then adding methyl acrylate and reacting at 40-65 DEG C for 1-3 hours. When 3-(methoxycarbonyl-methyl-amino)-methyl propionate is prepared, potassium trimethylsilanolate is used as a catalyst, so that the product yield can be increased.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a preparation method of 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester and an intermediate thereof. Background technique [0002] 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester is a commonly used intermediate for the synthesis of compounds. 3-(tert-butoxycarbonyl-methoxycarbonylmethyl-amino)-propionic acid methyl ester can be generated by reacting 3-(methoxycarbonylmethyl-amino)-propionic acid methyl ester with Boc anhydride. 3-(Methoxycarbonylmethyl-amino)-propionic acid methyl ester can be obtained by reacting glycine methyl ester hydrochloride with methyl acrylate. In the prior art, Unexpected Insertion of Nitrogen into aC-C Bond: Access to 2,3-Disstituted Quinazolinone Scaffolds (Liu, Hui-Li et al, Organic Letters, 23(12), 4579-4583; 2021) discloses glycine methyl Ester hydrochloride re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/22C07C227/08C07C229/16C07C227/40
CPCC07C269/04C07C227/08C07C227/40C07C271/22C07C229/16
Inventor 不公告发明人
Owner 郑州猫眼农业科技有限公司
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