Method for preparing pure enantio-methylpropane-2-sulfinamide

A technology of tert-butyl sulfinamide and tert-butyl sulfinyl, which is applied in the field of pharmaceutical synthesis, can solve the problems of high cost, unfavorable large-scale production, long overall steps, etc., and achieves reduction of reaction time, convenience for industrial scale-up production, Simple to use effects

Active Publication Date: 2018-09-21
安庆融创生物科技有限公司
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  • 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

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  • Method for preparing pure enantio-methylpropane-2-sulfinamide
  • Method for preparing pure enantio-methylpropane-2-sulfinamide
  • Method for preparing pure enantio-methylpropane-2-sulfinamide

Examples

Experimental program
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Embodiment 1

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

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

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

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Abstract

The invention discloses a method for preparing pure enantio-methylpropane-2-sulfinamide. The method comprises the following steps: carrying out selective oxidation on di-tert-butyl disulfide and hydrogen peroxide, reacting with an acylation reagent so as to obtain tert-butylsulfinyl chloride and tertiary butyl sulfonyl bromide, further reacting with hydrazine hydrate so as to obtain tertiary butylhydrazide, further carrying out resolution and separation with a DBTA resolving agent, and carrying out cracking with zinc acetate, thereby obtaining the pure enantio-methylpropane-2-sulfinamide. Themethod is simple, convenient and stable in process operation, high in yield and good in environment protection, and compared with a conventional process, the method is cheap and easy in raw materialobtaining, low in production cost of pure enantio-methylpropane-2-sulfinamide, and beneficial to industrial on-scale production.

Description

Technical field [0001] The invention belongs to the technical field of drug synthesis, and specifically relates to a method for preparing enantiopure tert-butylsulfinamide. Background technique [0002] Tert-butylsulfinamide, the English name is 2-methylpropane-2-sulfinamide, and the molecular formula is: (CH3)3CSONH2. Chiral tert-butylsulfinamide includes two chiral configurations, R-type and S-type. It is an important chemical used as a chiral prosthetic group. It is used in academic chiral synthesis, chiral drug synthesis and industry Both have important meanings and functions. [0003] Today, most drugs or drug intermediates have amine groups, which are important chiral prosthetic chemicals in asymmetric synthesis. Looking at recent academic reports and new drugs on the market, more and more drugs use enantiomerically pure tert-butylsulfinamide. For example, in academic reports, it is used in the synthesis of paclitaxel and the synthesis of anti-allergic drug cetirizine hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/06C07C313/04C07C313/02C07B57/00
CPCC07B57/00C07B2200/07C07C313/02C07C313/04C07C313/06
Inventor 高峰曾赛兰
Owner 安庆融创生物科技有限公司
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