139631-62-2

Usage

Uses

Used in Pharmaceutical Industry:
Cyclopropanesulfonyl chloride is used as a synthetic building block for the creation of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic sulfonamide derivatives. These derivatives are crucial in the development of potent hepatitis C virus NS3 protease inhibitors, which play a significant role in the treatment and management of hepatitis C.
The unique chemical properties of Cyclopropanesulfonyl chloride, such as its reactivity and stability, enable it to be a key component in the synthesis of these important pharmaceutical compounds, contributing to the advancement of treatments for hepatitis C and potentially other diseases.

InChI:InChI=1/C3H5ClO2S/c4-7(5,6)3-1-2-3/h3H,1-2H2

Upstream product

• 68846-57-1 (cyclopropyldisulfanyl)cyclopropane 
• 139631-61-1 cyclopropanesulfinyl chloride 
• 23719-80-4 cyclopropylmagnesium bromide 
• 154350-29-5 cyclopropanesulphonamide 

Downstream Products

• 146475-56-1 N-(p-tolyl)cyclopropanesulfonamide 
• 146475-51-6 propan-2-yl cyclopropanesulfonate 
• 146475-53-8 N,N-diethylcyclopropanesulfonamide 
• 154350-29-5 cyclopropanesulphonamide 
• 897919-50-5 C₂₈H₃₆FN₃O₄S 
• 908024-17-9 C₃₁H₄₉FN₄O₄S 
• 83635-12-5 1-butyl cyclopropanesulfonate 
• 879487-14-6 N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanesulfonamide 

Relevant academic research and scientific papers

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF4

Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF4), with nucleophiles. This simple reagent activates the poorly nucleophilic NH2 group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction conditions and the high selectivity of Pyry-BF4 towards NH2 groups permit the formation of sulfonyl chlorides in a late-stage fashion, tolerating a preponderance of sensitive functionalities.

HEPATITIS C INHIBITOR COMPOUNDS

Compounds of Formula (I): wherein B, R3, L0, L1, R2, Rc and R1 are defined herein. The compounds are useful as inhibitors of HCV NS3 protease for the treatment of hepatitis C viral infection. In particular, the present invention provides novel peptide analogs, pharmaceutical compositions containing such analogs, and uses of these analogs in the treatment of HCV infection

DIPHENYL-DIHYDRO-IMIDAZOPYRIDINONES

and the pharmaceutically acceptable salts and esters thereof X, R1, R2, Y1 and Y2 are described herein inhibit the interaction of MDM2 protein with a p53-like peptide and hence have anti proliferative activity.

Cyclopropanesulfonyl Chloride: Its Mechanism of Hydrolysis and Reactions with Tertiary Amines in Organic Media

Cyclopropanesulfonyl chloride (1) has been synthesized and its reactions examined to see if the three-membered ring leads to unusual reactions in either 1 or the corresponding sulfene, cyclopropanethione S,S-dioxide (2). pH-rate profiles, primary kinetic isotope effects (KIE's), and pH-product ratio experiments are in full agreement with mechanisms of hydrolysis of 1 like those of a simple alkanesulfonyl chlorides (J.Am.Chem.Soc.1992,114,1743-1749), specifically, (a) below pH 7.2 by SN2-S reaction with water and (b) above pH 7.3, elimination by hydroxide to form the sulfene (2) which is trapped by (i) water below pH 12.0 and (ii) hydroxide above pH 12.0.The products of the reaction of cyclopropanesulfonyl-1-d chloride (9) with triethylamine and 2-propanol in dichloromethane indicate that most of the reaction goes via 2; the analogous reaction with trimethylamine apparently proceeds by a direct formation of the sulfonylammonium chloride (14) which then yields the α-deuterated N,N-dimethyl sulfonamide (12, R=Me).The evident sulfene formation processes in the reaction of triethylamine with ethenesulfonyl, 2-propanesulfonyl, and cyclopropanesulfonyl chlorides show very low primary KIE's (1.5), pointing to highly product-like transition states.Reaction of 1 with an enamine (1-pyrrolidino-2-methylpropene, 20) in the presence of a base in either water or dichloromethane gave cyclopropanesulfonpyrrolidide (23) and an aldehyde adduct (24), but no four-membered cycloadduct (21).

In Pursuit of Cyclopropanethione: Cyclopropanethione S-Oxide and S,S-Dioxide

The geometries of cyclopropanethione (1a), methylenethiirane (2a), cyclopropanethione S-oxide (1b), methylenethiirane S-oxide (2b), cyclopropanethione S,S-dioxide (1c), methylenethiirane S,S-dioxide (2c), thioformaldehyde S,S-dioxide (sulfene), and the te