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Process for preparing Boc protected amino acid by (Boc) O

An amino acid and dicarbonic acid technology, which can be used in the preparation of cyanide reactions, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of taking too much time and failing to obtain good yields, shortening the reaction time, and reducing the The effect of contamination uniformity and simple reaction operation

Inactive Publication Date: 2006-06-28
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, when preparing Boc-protected L-aspartic acid ammonium and L-glutamic acid, people either use special reagents, such as: Boc-ODSP, Boc-N 3 etc., either need to spend too much time (> 12h), or need to control the pH value of the reaction solution, and often can not get a better yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add L-aspartic acid (20mmol) into the flask, add 4ml of water, 40ml of acetone, and add 2 equivalents of (CH 3 ) 3 N, control the temperature and add (Boc) under stirring at 0°C 2 O (22mmol), and continue to stir for 0.5h, evaporate the acetone under reduced pressure, extract the water layer with ethyl acetate (4×60ml), adjust the pH value of the water layer to 2-3 with dilute HCl, and extract with ethyl acetate (4×60ml), the combined organic layers were washed with saturated brine (2×10ml), anhydrous Na 2 SO 4 After drying, it was filtered and evaporated to dryness, and the obtained product was crystallized with ethyl acetate and petroleum ether (1:2, volume ratio) to obtain Boc-L-aspartic acid (60% yield).

Embodiment 2

[0027] Add L-glutamic acid (20mmol) into the flask, add 20ml of water, 40ml of acetone, add 2 equivalents of Et while stirring 3 N, control the temperature and add (Boc) under stirring at 25°C 2 O (22mmol), and continued to stir for 4h, distilled off acetone under reduced pressure, extracted the aqueous layer with ether (3×10ml), adjusted the pH value of the aqueous layer to 2-3 with dilute HCl, extracted with ethyl acetate (4× 60ml), the combined organic layers were washed with saturated brine (2×10ml), anhydrous Na 2 SO 4 After drying, it was filtered and evaporated to dryness, and the obtained product was crystallized with ethyl acetate and petroleum ether (1:2, volume ratio) to obtain Boc-L-glutamate (90% yield).

Embodiment 3

[0029] Add L-proline (20mmol) in the flask, add 40ml of water, 4ml of acetone, and add 1.5 equivalents of (CH 3 ) 3 N, control the temperature and add (Boc) under stirring at 40°C 2 O (22mmol), and continued to stir for 0.5h, evaporated the acetone under reduced pressure, adjusted the pH value of the obtained aqueous solution to 2-3 with dilute HCl, extracted with ethyl acetate (4×60ml), washed with saturated brine (2×10ml ), anhydrous Na 2 SO 4 After drying, it was filtered and evaporated to dryness, and the obtained product was crystallized with ethyl acetate and petroleum ether (1:2, volume ratio) to obtain Boc-L-proline (73% yield).

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PUM

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Abstract

The invention discloses a method that uses (Boc)2O to make amino acid of Boc protection. It uses acetone and water as solvent, under the existing of (Et3N), takes reaction to form amino acid of Boc protection. The invention has high yield, easy to produce and no pollution. The product has good homogeneity, high purity and low cost.

Description

technical field [0001] The invention discloses a (Boc) 2 O Processes for the preparation of Boc-protected amino acids, especially methods for the preparation of Boc-protected L-aspartic acid and L-glutamic acid. Background technique [0002] The common point of L-aspartic acid ammonium and L-glutamic acid is that they all contain carboxyl functional groups on the side chains. They are the cheapest and easily available amino acids among natural amino acids, and because of this, they are often used as chiral raw materials to design and synthesize some useful intermediates. When using them to synthesize and design, people often need to protect the amino group, and choosing a reasonable protecting group to protect the amino group has also become a difficult problem that people often face. As a better protecting group, Boc has been widely used in synthetic design, especially in peptide synthesis. However, so far, when preparing Boc-protected L-aspartic acid ammonium and L-glut...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/00C07C227/18C07C229/00C07C229/24
Inventor 胡先明滕汉兵魏海斌邱国福梁淑彩
Owner WUHAN UNIV
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