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Preparation method of tert-butyl 3-oxocyclobutyl carbamate

A technology of oxocyclobutylcarbamate and tert-butyl ester, applied in the field of medicine, can solve the problems of being unsuitable for industrial production, low yield and the like, and achieve the effects of low cost, high yield and mild reaction conditions

Active Publication Date: 2020-10-30
SYNCOZYMES SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] This route uses 3-methylenecyclobutylcarbanitrile as raw material, three-step reaction to obtain tert-butyl 3-oxocyclobutylcarbamate, the yield is extremely low, only 25%, and uses NaN 3 and other highly toxic reagents, not suitable for industrial production

Method used

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  • Preparation method of tert-butyl 3-oxocyclobutyl carbamate
  • Preparation method of tert-butyl 3-oxocyclobutyl carbamate
  • Preparation method of tert-butyl 3-oxocyclobutyl carbamate

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Embodiment 1

[0032] The preparation of embodiment 1 compound III

[0033] Add 50 g of compound IV to 200 mL of ethanol, then add 3.8 g of p-toluenesulfonic acid, cool to 0-5°C, add 79 g of triethyl orthoformate dropwise, and react at room temperature for 20 h after the drop is completed, and follow TLC until the reaction is complete. Extract and concentrate to dryness with dichloromethane, add 50mL methyl tert-butyl ether to make a slurry, filter, wash, and dry to obtain 75g of white solid with a yield of 91% and a purity of 98%. 1 For H NMR data see figure 1 .

Embodiment 2

[0034] The preparation of embodiment 2 compound III

[0035] Add 50 g of compound IV to 200 mL of ethanol, then add 2.2 g of concentrated sulfuric acid, cool to 0-5°C, add 79 g of triethyl orthoformate dropwise, and react at room temperature for 20 h after the drop is completed, followed by TLC until the reaction is complete. Extract and concentrate to dryness with dichloromethane, add 50mL methyl tert-butyl ether to make a slurry, filter, wash, and dry to obtain 71g of white solid with a yield of 86% and a purity of 98%.

Embodiment 3

[0036] The preparation of embodiment 3 compound III

[0037] Add 50g of compound IV to 200mL of methanol, then add 3.8g of p-toluenesulfonic acid, cool to 0-5°C, slowly add 57g of trimethyl orthoformate dropwise, and react at room temperature for 20h after the drop is completed, and follow TLC until the reaction is complete. Extract and concentrate to dryness with dichloromethane, add 50 mL of methyl tert-butyl ether to make a slurry, filter, wash, and dry to obtain 62 g of white solid with a yield of 88% and a purity of 98%.

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of tert-butyl 3-oxocyclobutyl carbamate (I). The method comprises the following steps: protecting a compound IV to generate a compound III, carrying out Hofmann degradation reaction to obtain a compound II, and finally, carrying out deprotection to obtain a compound I. Compared with the prior art, the method is low in technical route cost and mild in reaction condition, avoids the use of toxic reagents with larger danger coefficients, is green and environment-friendly, and has good application value.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation method of tert-butyl 3-oxocyclobutylcarbamate. Background technique: [0002] As an important molecular skeleton, aminocyclobutane is widely used in the design of new drug molecules, such as drugs for the treatment of hepatitis C virus infection (WO2013064538); LSD1 inhibitors containing aminocyclobutane skeletons (WO2013057322); JAK and SYK inhibitors of butane (WO2013030138); 1,3-cyclobutanediamine containing aminocyclobutane (CN104829492); Ivonib intermediates containing aminocyclobutane (WO2015010297, WO2013107291 and WO2013107405). And tert-butyl 3-oxocyclobutylcarbamate (CAS No.: 154748-49-9) with aminocyclobutane structure is an important intermediate for the synthesis of such compounds. Some documents have publicly reported the synthetic method of tert-butyl 3-oxocyclobutylcarbamate at present. [0003] Patents WO2015010297, WO2013107291 and ...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/20
CPCC07C221/00C07C213/08C07C231/12C07C2601/04C07C225/20C07C217/52C07C235/40Y02P20/55
Inventor 竺伟袁利
Owner SYNCOZYMES SHANGHAI
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