Process method for synthetizing tert-butyl sulfinamide

Abstract

The invention relates to a method for synthetizing an organic compound. A process method for synthetizing tert-butyl sulfinamide comprises the following steps: (a) under the temperature of between 50 DEG C below zero to 70 DEG C below zero, adding triphenyl methyl halide into liquid ammonia to obtain N methyl triphenyl ammonia; (b) under the temperature of between 60 DEG C below zero and 70 DEG Cbelow zero, adding n-butyl lithium into organic solution of N methyl triphenyl ammonia to obtain organic solution of N methyl (triphenyl) lithium amide; (c) at the temperature of between 50 DEG C below zero and 70 DEG C below zero, dropwise adding organic solution of (S)-tert-butyl sulfinic acid tert-butyl thioester into the N-methyl (triphenyl) lithium amide, quenching the mixture by using water, carrying out deodorization by using dimethyl sulfate, destroying excessive dimethyl sulfate by using ammonia and carrying out post treatment to obtain (S)-N-methyl (triphenyl) tert-butyl sulfinamide; and (d) taking the product in the step (c), adding dilute acid into the product, adjusting the pH value of the mixture to 3, neutralizing the mixture by using alkaline solution until the pH value isbetween 13 and 14 and carrying out post treatment to obtain (S)-tert-butyl sulfinamide. The process method for synthetizing the tert-butyl sulfinamide has simple and convenient operation and good process stability, avoids copious cooling at the low or ultralow temperature, reduces the using amount of ammonia, removes foul odour and is easy to realize industrial production.

Description

A kind of processing method of synthesizing tert-butylsulfinamide 1. Technical field The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing tert-butylsulfinamide. 2. Background technology: More than 75% of the drugs and drug candidates have ammonia functional groups. Nevertheless, the development of asymmetric ammonia is much later than that of other common functional group asymmetric synthesis. In recent years, tert-butyl sulfinamide has attracted more and more attention and application in asymmetric synthesis. In drug synthesis, tert-butyl sulfinamide is introduced on the aromatic ring, [References: Dembowski, Udo; Noltemeyer , Mathias; Gilje, John W.; Roesky, Herbert W.; CHBEAM; Chem.; 1991, 124, 1917-1922]; 2001, 40, 4544.]. In recent years, there have been literatures on the synthesis of (S)-tert-butylsulfinamide. as follows: Use commercially available tetrahydrofuran solution of (S or R)-tert-butylsulfini...

AI Technical Summary

Problems solved by technology

These unfavorable reaction characteristics limit the large-scale industrial synthesis of (S or R)-tert-butylsulfinamide, so looking for a synthetic process that can avoid cryogenic ultra-low temperature, reduce the amount of ammonia gas, remove foul smell, and be suitable for industrial production is very necessary