Method of synthesizing enantiomerically pure tert-butanesulfinamide

A technology of tert-butyl sulfinamide and tert-butyl sulfinyl, applied in the field of pharmaceutical synthesis, can solve the problems of high cost, long overall steps, unfavorable large-scale production, etc., and achieves reduced reaction time, simple operation, and convenient industrialization. Amplify the effect of production

Active Publication Date: 2018-08-17
大连双硼医药化工有限公司
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In the above method, the production of tert-butyl mercaptan with bad smell is not involved, but the cost is high and the overall steps are long, which is not conducive to large-scale production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method of synthesizing enantiomerically pure tert-butanesulfinamide
  • Method of synthesizing enantiomerically pure tert-butanesulfinamide
  • Method of synthesizing enantiomerically pure tert-butanesulfinamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The first step: the synthesis of tert-butyl thiosulfinate.

[0043] (1) Add 180g tert-butyl disulfide, 1.8gVO(acac)2 and 400mL ethanol successively in the reaction bottle, add 138.5g 27% hydrogen peroxide dropwise at 25°C, react at 30-35°C for 7 hours, take a sample for TLC or According to HPLC detection, the raw material is less than 1.5%, concentrated under reduced pressure, washed once with saturated sodium chloride water, then added 400 g of dichloromethane to dilute sodium sulfate and dried for later use. The external standard yield was 88%.

[0044] (2) Add 180g of tert-butyl disulfide and 420mL of acetic acid in turn to the reaction bottle, add 150.1g of 27% hydrogen peroxide dropwise at 25°C, react at 30-35°C for 3 hours, take a sample for TLC or HPLC detection, and the raw material is less than 1% , then poured into 500g of water, extracted with dichloromethane, washed once with saturated sodium chloride water, dried over sodium sulfate for use. The external ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a method of synthesizing enantiomerically pure tert-butanesulfinamide. The method comprises the following steps of using tert-butyl disulfide and hydrogen peroxide for selective oxidation, then performing reaction on a product and an acylation reagent to obtain tert-butylsulfinyl chloride or tert-butylsulfinyl bromide, then performing reaction on the tert-butylsulfinyl chloride or the tert-butylsulfinyl bromide and hydrazine hydrate to obtain tert-butylsulfinyl hydrazine, then performing reaction on the tert-butylsulfinyl hydrazine and a DTTA resolving agent for resolution and dissociation, and performing zinc / acetic acid pyrolysis to obtain the enantiomerically pure tert-butanesulfinamide. The method provided by the invention is simple, convenient and stable in technological operation and high in yield, is environmentally friendly, is cheap and available in raw materials compared with the prior art, lowers the production cost of the existing enantiomerically pure tert-butanesulfinamide and is beneficial to industrialized mass production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a method for synthesizing enantiopure tert-butylsulfinamide. Background technique [0002] Tert-butylsulfinamide, the English name is 2-methylpropane-2-sulfinamide, the molecular formula is: (CH3)3CSONH2. Chiral tert-butyl sulfinamide includes two chiral configurations of R type and S type. It is an important chemical as a chiral prosthetic group. It is widely used in academic chiral synthesis, chiral drug synthesis and industry are of great significance and function. [0003] Nowadays, most drugs or drug intermediates have amine groups, which are important chiral prosthetic chemicals in asymmetric synthesis. Looking at recent academic reports and marketed new drugs, there are more and more drugs using enantio-pure tert-butylsulfinamide. For example, it has been used in the synthesis of paclitaxel and the synthesis of antiallergic drug cetirizine hydroch...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/06C07C313/04
CPCC07C313/04C07C313/06
Inventor 高峰曾赛兰
Owner 大连双硼医药化工有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap