1218918-76-3

Basic information

• Product Name: dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate
• Synonyms: dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate
• CAS NO: 1218918-76-3
• Molecular Weight: 319.311
• Mol File: 1218918-76-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate(1218918-76-3)
• EPA Substance Registry System: dimethyl (2R)-2-[[(4-fluorophenyl)sulfonyl]amino]-butanedioate(1218918-76-3)

Safety Data

• Hazardous Substances Data: 1218918-76-3(Hazardous Substances Data)

Upstream product

• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 6384-18-5 dimethyl D-aspartate 
• 14358-33-9 dimethyl (R)-2-aminobutanedioate hydrochloride 
• 32213-95-9 dimethyl L-aspartate hydrochloride 

Downstream Products

• 1218918-77-4 N-[(2R)-1,4-dihydroxybutan-2-yl]-4-fluorobenzenesulfonamide 
• 1218918-78-5 2-[(2R)-1-[(4-fluorophenyl)sulfonyl]aziridin-2-yl]ethanol 
• 1271732-14-9 C₂₀H₂₀FN₃O₅S 
• 1360470-68-3 methyl (2R)-2-(1-[2-[4-fluoro-N-methylphenylsulfonamido]-4-hydroxybutyl]-1H-indol-3-yl)acetate 
• 1218918-82-1 C₂₂H₂₃FN₂O₅S 
• 1218918-80-9 C₂₈H₃₉FN₂O₅SSi 
• 1218918-65-0 methyl [(7R)-7-[[(4-fluorophenyl)sulfonyl](methyl)amino]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate 
• 1218918-62-7 [3H]-MK-7246 

Relevant articles and documents

CRTH2 antagonist MK-7246: A synthetic evolution from discovery through development

In this paper, we report the development of different synthetic routes to MK-7246 (1) designed by the Process Chemistry group. The syntheses were initially designed as an enabling tool for Medicinal Chemistry colleagues in order to rapidly explore structure-activity relationships (SAR) and to procure the first milligrams of diverse target molecules for in vitro evaluation. The initial aziridine opening/cyclodehydration strategy was also directly amenable to the first GMP deliveries of MK-7246 (1), streamlining the transition from milligram to kilogram-scale production needed to support early preclinical and clinical evaluation of this compound. Subsequently a more scalable and cost-effective manufacturing route to MK-7246 (1) was engineered. Highlights of the manufacturing route include an Ir-catalyzed intramolecular N-H insertion of sulfoxonium ylide 41 and conversion of ketone 32 to amine 31 in a single step with excellent enantioselectivity through a transaminase process. Reactions such as these illustrate the enabling impact and efficiency gains that innovative developments in chemo- and biocatalysis can have on the synthesis of pharmaceutically relevant target molecules.

Discovery of MK-7246, a selective CRTH2 antagonist for the treatment of respiratory diseases

In this manuscript we wish to report the discovery of MK-7246 (4), a potent and selective CRTH2 (DP2) antagonist. SAR studies leading to MK-7246 along with two synthetic sequences enabling the preparation of this novel class of CRTH2 antagonist are reported. Finally, the pharmacokinetic and metabolic profile of MK-7246 is disclosed.

INDOLE DERIVATIVES AS CRTH2 RECEPTOR ANTAGONISTS

The compound (+) {7R-[[(4-fluorophenyl)sulfonyl](methyl)ammo]-6,7,8,9-tetrahydropyrido[1,2-a]mdol-10-yl}acetic acid and pharmaceutically acceptable salts thereof are antagonists of the PGD2 receptor, CRTH2, and as such are useful in the treatment and/or prevention of CRTH2-meidated diseases such as asthma.