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Method for synthesizing chiral optical pure para-toluene sulfenamide

A technology of toluene sulfinamide and sodium toluene sulfinate, which is applied in the field of drug synthesis, can solve the problems of high price of LiHMDS, large solvent ratio, unfavorable large-scale production, etc., achieve high atom utilization, improve alkalinity, and save costs Effect

Active Publication Date: 2018-09-04
浙江凯普化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In the above method, the price of LiHMDS used is higher, and the proportion of solvent used is relatively large, and it is only effective for (S)-p-toluene sulfinamide, which is not conducive to large-scale production

Method used

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  • Method for synthesizing chiral optical pure para-toluene sulfenamide
  • Method for synthesizing chiral optical pure para-toluene sulfenamide
  • Method for synthesizing chiral optical pure para-toluene sulfenamide

Examples

Experimental program
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Embodiment 1

[0041] The first step: the synthesis of p-toluenesulfinyl chloride.

[0042] (1) Put 267g of toluene, 53.4g of sodium p-toluene sulfinate and 0.1g of N,N-dimethylformamide into a dry and clean 500mL four-necked bottle with an addition funnel, add 57.5g of thionyl chloride dropwise at room temperature, React at 55-65°C for 4 hours, take samples for GC or HPLC detection after derivatization, the raw material is less than 0.3%, concentrate under reduced pressure, replace once with 150g of toluene, then add 50g of toluene to dilute for later use. The external standard yield is 94%.

[0043] (2) Put 267g of benzene, 53.4g of sodium p-toluenesulfinate and 0.1g of N,N-dimethylformamide into a dry and clean 500mL four-necked bottle with an addition funnel, add 57.5g of thionyl chloride dropwise at room temperature, and Reaction at 55-65°C for 4 hours, sampled by GC or HPLC after derivatization, the raw material is less than 0.3%, concentrated under reduced pressure, replaced once wit...

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Abstract

The invention discloses a method for synthesizing chiral optical pure para-toluene sulfonamide. The method comprises the following steps: ensuring that para-toluene sulfinic acid sodium salt and an acylating chlorination reagent react with each other, so as to obtain para-toluene sulfenyl chlorine, then ensuring that the para-toluene sulfenyl chlorine reacts with hydrazine hydrate, so as to obtainpara-toluene sulfenyl hydrazine, performing split resolving through a DTTA resolving agent, and performing zinc acetate splitting to obtain corresponding pure para-toluene sulfonamide. The method issimple, convenient and stale to operate, high in yield, and environmentally friendly, and compared with the prior art, the method has the advantages that raw materials are cheap and available, the production cost of the conventional chiral optical pure para-toluene sulfonamide is greatly reduced, and the method is beneficial to industrial scale production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a method for synthesizing chiral optically pure p-toluene sulfinamide. Background technique [0002] p-toluenesulfinamide, the English name is p-toluenesulfinamide, the molecular formula is: C7H9NOS. Including R-type and S-type configurations, the English names correspond to (R)-p-toluenesulfinamide and (S)-p-toluenesulfinamide respectively. Since it was first synthesized in the middle of last century, it has been used as one of the key chiral sources of chiral amine drugs and their intermediates. Especially widely in academics, it is an important chemical as a chiral prosthetic group, which is of great significance in chiral synthesis and chiral drug synthesis. Nowadays, most of the drugs or drug intermediates have amine groups, and in many reports, chirally optically pure p-toluenesulfinamides are a flexible source of diastereomers in asymmetric synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/06
CPCC07B2200/07C07C51/412C07C303/02C07C303/36C07C303/44C07C313/06C07C309/86C07C311/49C07C59/255
Inventor 高峰曾赛兰
Owner 浙江凯普化工有限公司