1414932-72-1

Basic information

• Product Name: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one
• Synonyms: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one
• CAS NO: 1414932-72-1
• Molecular Weight: 413.861
• Mol File: 1414932-72-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one(1414932-72-1)
• EPA Substance Registry System: 4-{4-[(S)-5-[(((4-chlorophenyl)methylene)amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}-morpholin-3-one(1414932-72-1)

Safety Data

• Hazardous Substances Data: 1414932-72-1(Hazardous Substances Data)

Upstream product

• 1325210-64-7 4-(4-isocyanatophenyl)morpholin-3-one 
• 1345879-85-7 (S)-(E,Z)-N-4-chlorobenzylidene-1-(oxiran-2-yl)methanamine 
• 1345879-87-9 (S)-1-chloro-3-{[(4-chlorophenyl)methylene]amino}propan-2-ol 
• 1414932-71-0 dodecyl (4-(3-oxomorpholin)phenyl)carbamate 
• 1313613-18-1 [4-(3-oxo-morpholin-4-yl)phenyl]carbamic acid benzyl ester 
• 438056-69-0 4-(4-aminophenyl)morpholin-3-one 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 366789-02-8 Rivaroxaban 
• 446292-10-0 4-[4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholine-3-one 
• 1251952-62-1 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one methanesulfonic acid salt 

Relevant articles and documents

A Convenient Synthesis of Rivaroxaban from (S)-Epichlorohydrin

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PROCESS FOR OBTAINING RIVAROXABAN AND INTERMEDIATE THEREOF

This invention relates to a procedure for obtaining a thiophene-2-carboxamide compound, specifically rivaroxaban, which comprises the (i) fragmentation of the N═C bond of a compound of formula 23 where R1 is selected among hydrogen, halogen, and (C1-C6)alkyl; and (ii) acylation of the resulting intermediate with 5-chloro-tiofen-2-carbonyl chloride in a solvent medium, in the presence of a base. The invention also relates to the compounds of formula 23 and their use in the obtention of rivaroxaban.

A PROCESS FOR THE PREPARATION OF RIVAROXABAN BASED ON THE USE OF (S)-EPICHLOROHYDRIN

The invention relates to the stereoisomers of 4-{4-[(S/R)-5-[(((aryl)methylene)- amino)methyl]-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-ones described by the chemical formulae (S)-(9) and (R)-(9). The optical isomer of compound (9) with the (S)- configuration is industrially applicable for the manufacture of the antithrombotic drug rivaroxaban (1). The new preparation process of rivaroxaban comprises a reaction of (S)-1- chloro-3-(((aryl)methylene)amino)propan-2-ols (S)-(14) with alkyl 4-(3-oxomorpholine-4- yl)phenylcarbamates (15) providing the key intermediate (S)-(9), which is further subjected to hydrolytic deprotection and subsequent acylation, producing rivaroxaban. The commercially available (S)-epichlorohydrin has been conveniently used as the chiral building block for the production of the key intermediate.