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Preparation method of chiral optical pure p-toluenesulfinamide

A technology of toluene sulfinamide and sodium toluene sulfinate, which is applied in the field of preparation of chiral optical pure p-toluene sulfinamide, can solve the problems of high price of LiHMDS, large solvent ratio, unfavorable large-scale production, etc., and achieve atom utilization High efficiency, improved alkalinity, and cost-saving effects

Active Publication Date: 2018-08-24
SHANGHAI TIANYE CHEM
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  • 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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  • Preparation method of chiral optical pure p-toluenesulfinamide
  • Preparation method of chiral optical pure p-toluenesulfinamide
  • Preparation method of chiral optical pure p-toluenesulfinamide

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Embodiment 1

[0042] The first step: the synthesis of p-toluenesulfinyl chloride.

[0043] (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%.

[0044] (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 preparation method of a chiral optical pure p-toluenesulfinamide. The method includes: subjecting sodium p-tolylsulfinate and an acyl chlorination reagent to acyl chlorination to obtain p-toluene sulfinyl chloride, then reacting the p-toluene sulfinyl chloride with hydrazine hydrate to obtain p-toluene sulfinyl hydrazine, then subjecting the p-toluene sulfinyl hydrazine and a DBTA resolving agent to resolution dissociation, and then performing zinc / acetic acid cracking to obtain enantiomerically pure p-toluenesulfinamide. The process provided by the invention has thecharacteristics of simple and stable operation, high yield, and environmental friendliness, and compared with the prior art, the raw materials are cheap and easily available, and the production cost of the existing chiral optical pure p-toluenesulfinamide is greatly reduced, therefore the method is beneficial to industrial mass production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a preparation method of 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 synthesis...

Claims

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Application Information

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IPC IPC(8): C07C313/06
CPCC07B2200/07C07C313/02C07C313/06
Inventor 高峰曾赛兰
Owner SHANGHAI TIANYE CHEM
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