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Preparation method of chiral beta-(Boc-amino)-5-hexynoic acid

A hexynoic acid and amino technology, applied in the field of preparation of chiral β--5-hexynoic acid, can solve the problems of high production cost and complicated preparation process

Active Publication Date: 2021-05-11
上海海皋科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the binaphthazobenzene photosensitive cyclic chiral molecule prepared by this technology is easy to synthesize and has good stability, the preparation process is complicated and the production cost is high

Method used

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  • Preparation method of chiral beta-(Boc-amino)-5-hexynoic acid
  • Preparation method of chiral beta-(Boc-amino)-5-hexynoic acid
  • Preparation method of chiral beta-(Boc-amino)-5-hexynoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088]A method of preparation of (R) -β- (BOC-amino) -5-hexynone acid, specifically, including the steps of:

[0089](1)

[0090](R) -α- (BOC-amino) -4-pentanylic acid (1.5 g, 7.035 mmol) and triethylamine (0.93 g, 9.145 mmol) were added to 10 ml of tetrahydrofuran, under nitrogen protection, at 0 ° C Ethyl chloroformate (0.992 g, 9.145 mmol) was dripped, and after the dropwise addition was completed, 60 min was reacted at 0 ° C to obtain a product.Resulting productUnstable, no purification is required to directly carry out the next step.

[0091](2)

[0092]At -15 ° C, the isopropyl ether solution (38.69 mL) (38.69 mL) of a diazomethane (38.69 mL) drop gravy concentration of 1 mol / L was obtained from step (1), and under the condition of -15 ° C, the reaction was 20 min; heated to At 0 ° C, a acetic acid solution (21.12 g) of a 12% percentage of a mass of 10% was added dropwise, and the reaction was 30 min under 0 ° C.There is no need to purify directly into the next step.

[0093](3)

[0094]At -5...

Embodiment 2

[0099]A method of preparation of (S) -β- (BOC-amino) -5-hexynum acid, specifically, including the steps of:

[0100](1)

[0101](S) -α- (BOC-amino) -4-pentanylic acid (1.8 g, 8.441 mmol) and N-methylmorpholine (1.02 g, 10.13 mmol) were added to 10 ml of methyl tert-butyl ether, Under argon, Ethyl chloroformate (1.099 g, 10.13 mmol) was added dropwise to -5 ° C, and the reaction was added to 2 ° C for 55 min.Resulting productUnstable, no purification is required to directly carry out the next step.

[0102](2)

[0103]At -13 ° C, a methyl tert-butyl ether solution (63.91 mL) dropped to the reaction solution to the reaction liquid, and under the condition of -13 ° C, the reaction is obtained from the step (1). 15 min; heated to -3 ° C, a propionic acid solution (33.11 g) of 10% by weight of mass was added dropwise, and the reaction was 32 min under the condition of -3 ° C to obtain a productThere is no need to purify directly into the next step.

[0104](3)

[0105]At -3 ° C, the reaction solution obta...

Embodiment 3

[0109]A method of preparation of (R) -β- (BOC-amino) -5-hexynone acid, specifically, including the steps of:

[0110](1)

[0111](R) -α- (BOC-amino) -4-pentanylic acid (2 g, 9.38 mmol) and N, N-diisopropylethylamine (1.33 g, 10.32 mmol) were added to 10 ml of tetrahydrofuran, in nitrogen Under the protected, Ethyl chloroformate (1.272 g, 11.72 mmol) was dripped at -3 ° C, and after the dropwise addition was completed, the reaction was 10 min to obtain a product.Resulting productUnstable, no purification is required to directly carry out the next step.

[0112](2)

[0113]At -12 ° C, the isopropyl ether solution (52.11 mL) of aidazole concentration of 0.9 mol / L is obtained from the step (1), and the reaction is 18 min under the condition of -12 ° C; temperature rise By 5 ° C, a acetic acid solution (28.16 g) of 10% by weight of mass was added dropwise, and the reaction was 35 min under the conditions of 5 ° C.There is no need to purify directly into the next step.

[0114](3)

[0115]At 5 ° C, the r...

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Abstract

The invention provides a preparation method of chiral beta-(Boc-amino)-5-hexynoic acid. The preparation method comprises the following steps of: (1) carrying out carboxyl activation reaction on chiral alpha-(Boc-amino)-4-pentynoic acid and chloroformate to obtain a compound as shown in a formula I; (2) carrying out substitution reaction on the compound as shown in the formula I obtained in the step (1) and diazomethane to obtain a compound as shown in a formula II; (3) carrying out Wolff rearrangement reaction on the compound as shown in the formula II obtained in the step (2) in the presence of an alkaline substance to obtain a compound as shown in a formula III; and (4) carrying out acidification reaction on the compound as shown in the formula III obtained in the step (3) to obtain a target product. The raw materials in the preparation method are easy to obtain, the reaction conditions are mild, and the preparation method is suitable for industrial large-scale production.

Description

Technical field[0001]The invention belongs to the art of organic compound synthesis, and is specifically related to the preparation method of chiral β- (BOc-amino) -5-hexynone acid.Background technique[0002]When the carbon atom is formed, four atoms or groups can form three-dimensional spatial structures by four covalent bonds. Due to the different atoms or groups, two molecular structures can be formed, referred to as chiral molecules. The chiral molecules are mirrored in chemical structures but cannot be completely coincident after any rotation, just like left hands and right hand, therefore also referred to as chiral isomers, and there is often different differences between drug power, toxicity, etc. Even the opposite, so more and more methods are applied to the preparation of chiral molecules.[0003]CN 102442981A discloses a split method of γ-dode-deridative halodynogenic molecules. The technique removes the γ-dodeol in alkaline conditions into a hydroxy acid, and the use of opti...

Claims

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Application Information

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IPC IPC(8): C07C269/06C07C269/08C07C271/22C07C271/20
CPCC07C269/06C07C269/08C07B2200/07C07C271/22C07C271/20Y02P20/55
Inventor 李海鹏孙开
Owner 上海海皋科技有限公司
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