t-Butyl(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate

Base Information

• Chemical Name: t-Butyl(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate
• CAS No.: 630421-48-6
• Molecular Formula: C14H22N2O5S
• Molecular Weight: 330.405
• Mol file: 630421-48-6.mol

Synonyms:tert-Butyl N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamate;

Chemical Property of t-Butyl(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate

Chemical Property:

• Refractive Index: 1.547
• PKA: 4.68±0.40(Predicted)
• PSA: 116.93000
• Density: 1.299 g/cm³
• LogP: 3.18970

Purity/Quality:

98% ^*data from raw suppliers

T-butyl(1r,2s)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of t-Butyl(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate

There total 16 articles about t-Butyl(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

cyclopropanesulphonamide (154350-29-5) + (1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid (159622-10-3,213316-50-8,259221-77-7) → tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate (630421-48-6)

Guidance literature:

With 1,1'-carbonyldiimidazole; at 20 ℃; Reflux;

DOI:10.1021/jm401840s

Reference yield: 97.0%

→ tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate (630421-48-6)

Guidance literature:

Reference yield: 92.0%

cyclopropanesulphonamide (154350-29-5) → tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate (630421-48-6)

Guidance literature:

(1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 0.833333h; Heating / reflux;

cyclopropanesulphonamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 20h;

With hydrogenchloride; In tetrahydrofuran; water; pH=1;

upstream raw materials:

cyclopropanesulphonamide

(1R,2S)-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylic acid

N-Boc-(1R,2S)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester

ethyl acetate

Downstream raw materials:

(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropane-1-carboxamide

(1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride

C₃₈H₄₀N₄O₈S

C₃₁H₃₃ClN₄O₇S

Refernces

• 1、 -. "Macrocyclic compounds for suppressing replication of hepatitis C virus". Page/Page column 41. . Retrieved 2016/05/24.
• 2、 Scola, Paul M.,Wang, Alan Xiangdong,Good, Andrew C.,Sun, Li-Qiang,Combrink, Keith D.,Campbell, Jeffrey A.,Chen, Jie,Tu, Yong,Sin, Ny,Venables, Brian L.,Sit, Sing-Yuen,Chen, Yan,Cocuzza, Anthony,Bilder, Donna M.,D'Andrea, Stanley,Zheng, Barbara,Hewawasam, Piyasena,Ding, Min,Thuring, Jan,Li, Jianqing,Hernandez, Dennis,Yu, Fei,Falk, Paul,Zhai, Guangzhi,Sheaffer, Amy K.,Chen, Chaoqun,Lee, Min S.,Barry, Diana,Knipe, Jay O.,Li, Wenying,Han, Yong-Hae,Jenkins, Susan,Gesenberg, Christoph,Gao, Qi,Sinz, Michael W.,Santone, Kenneth S.,Zvyaga, Tatyana,Rajamani, Ramkumar,Klei, Herbert E.,Colonno, Richard J.,Grasela, Dennis M.,Hughes, Eric,Chien, Caly,Adams, Stephen,Levesque, Paul C.,Li, Danshi,Zhu, Jialong,Meanwell, Nicholas A.,McPhee, Fiona. "Discovery and early clinical evaluation of BMS-605339, a potent and orally efficacious tripeptidic acylsulfonamide ns3 protease inhibitor for the treatment of hepatitis C virus infection". . p. 1708 - 1729. Retrieved 2014/04/03.