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Method for preparing (2S)-2-[[(9H-fluorene-9-yl methoxy) carbonyl] amino]-3-(2,2-dimethyl-1,3-benzo dioxol-5-yl)propionate

A technology of benzodioxol and methoxy, which is applied in the direction of organic chemistry, can solve the problems of many steps in the synthesis route and difficult operation, and achieve the effect of simple operation, relaxed reaction conditions, and easy operation

Active Publication Date: 2013-12-25
GL BIOCHEM SHANGHAI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to provide a kind of (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(2,2-dimethyl-1,3-benzo The preparation method of dioxol-5-yl)propionic acid mainly solves the technical problems of many existing synthetic routes and difficult operation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Mix levodopa and sodium bicarbonate at a molar ratio of 1:4, add water and stir, add acetone and stir, add fluorenylmethoxycarbonyl succinimide with a molar ratio of levodopa of 1:0.95, stir overnight, and remove by rotary evaporation Wash the water layer with acetone and ether, add ethyl acetate, adjust the pH to 4, separate, extract, wash the ethyl acetate layer with water, dry, concentrate, add petroleum ether to crystallize, filter, and dry to obtain fluorenyl moxycarbonyl bar.

[0012] The reaction of fluorenylmethoxycarbonyl levodopa with 2,2-dimethoxypropane generates (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(2, The operation steps of 2-dimethyl-1,3-benzodioxol-5-yl)propionic acid are as follows, fluorenylmethoxycarbonyl levodopa is dissolved in tetrahydrofuran, and the molar ratio of 1:10 is added to 2 , 2-dimethoxypropane, add pyridinium p-toluenesulfonate with a molar ratio of 1:0.2, reflux for 8 hours, concentrate THF after reaction, add ethyl ace...

Embodiment 2

[0015] Mix 1 mol of levodopa, 5 mol of sodium bicarbonate, and solids evenly, add 3 liters of water and stir, add 2.5 liters of acetone, stir, slowly add 0.95 mol of fluorenyl moxycarbonyl succinimide, stir overnight, rotary steam, remove acetone, A large amount of viscous solids precipitated. Add 1 liter of diethyl ether, stir vigorously for 5 minutes, and separate the liquids. Add 2 liters of ethyl acetate to the water layer, stir, and adjust the pH value of the water layer to 3 with 3 equivalents of hydrochloric acid. The system is clarified, and the liquids are separated. The aqueous layer was extracted once more with 1 liter of ethyl acetate, the ethyl acetate layers were combined, washed once with 1 N hydrochloric acid, once with water, twice with saturated brine, dried over anhydrous sodium sulfate, and filtered to remove Sodium sulfate water, concentrated ethyl acetate layer, washed the solid with petroleum ether, filtered off the solid, and dried to obtain 0.9 mol o...

Embodiment 3

[0018] Mix 1 mol of levodopa, 4 mol of sodium bicarbonate, and solids evenly, add 3 liters of water and stir, add 2.5 liters of acetone, stir, slowly add 0.9 mol of fluorenyl moxycarbonyl succinimide, stir overnight, rotary steam, remove acetone, A large amount of viscous solids precipitated. Add 1 liter of diethyl ether, stir vigorously for 5 minutes, and separate the liquids. Add 2 liters of ethyl acetate to the water layer, stir, and adjust the pH value of the water layer to 3 with 3 equivalents of hydrochloric acid. The system is clarified, and the liquids are separated. The aqueous layer was extracted once more with 1 liter of ethyl acetate, the ethyl acetate layers were combined, washed once with 1 N hydrochloric acid, once with water, twice with saturated brine, dried over anhydrous sodium sulfate, and filtered to remove Sodium sulfate water, concentrate the ethyl acetate layer, wash the solid with petroleum ether, filter out the solid, and dry to obtain 0.85mol of the...

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Abstract

The invention discloses a method for preparing (2S)-2-[[(9H-fluorene-9-yl methoxy) carbonyl] amino]-3-(2,2-dimethyl-1,3-benzo dioxol-5-yl)propionate, which mainly aims to solve the technical problems of complicated steps and high operating difficulty in existing synthetic routes. The invention has the technical scheme that levodopa reacts with Fmoc N-hydroxysuccinimide este to obtain Fmoc acyl levodopa; and the Fmoc acyl levodopa reacts with 2,2-dimethoxypropane to obtain (2S)-2-[[(9H-fluoren-9-yl methoxy) carbonyl] amino]-3-(2,2-dimethyl-1,3- benzo dioxol-5-yl)propionate. The solvent used in the reaction of the Fmoc acyl levodopa and the 2,2-dimethoxypropane to obtain the (2S)-2-[[(9H-fluoren-9-yl methoxy) carbonyl] amino]-3-(2,2-dimethyl-1,3- benzo dioxol-5-yl)propionate is tetrahydrofuran; and the catalyst is pyridinium p-toluenesulfonate. The resultant obtained by the method is applied in the field of peptide synthesis as a non-natural amino acid protecting reagent.

Description

technical field [0001] The present invention relates to compound (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(2,2-dimethyl-1,3-benzodioxol- 5-base) the preparation method of propionic acid. Background technique [0002] Compound (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(2,2-dimethyl-1,3-benzodioxol-5-yl ) Propionic acid is a non-natural amino acid protection reagent used in the field of peptide synthesis. In the published US patent US 2010 / 0087622 A1, its synthesis involves seven steps, and the operation is relatively difficult. The present invention improves the synthetic route. Contents of the invention [0003] The object of the present invention is to provide a kind of (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(2,2-dimethyl-1,3-benzo The preparation method of dioxol-5-yl)propionic acid mainly solves the technical problems of many steps and difficult operation in the existing synthetic route. [0004] The technical solution of the present i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/46
Inventor 徐红岩李忠亮饭岛悠介
Owner GL BIOCHEM SHANGHAI
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