204386-76-5

Basic information

• Product Name: 4-Oxazolidinecarboxamide, 5-methyl-N-[(1S)-2-[(2R)-2-methyl-1-pyrrolidinyl]-2-oxo-1-(4-thiazolylmethyl)ethyl]-2-oxo-, (4S,5S)-
• Synonyms: 4-Oxazolidinecarboxamide, 5-methyl-N-[(1S)-2-[(2R)-2-methyl-1-pyrrolidinyl]-2-oxo-1-(4-thiazolylmethyl)ethyl]-2-oxo-, (4S,5S)-;Rovatirelin
• CAS NO: 204386-76-5
• Molecular Formula: C16H22N4O4S
• Molecular Weight: 366.43528
• Mol File: 204386-76-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 755.1±60.0 °C(Predicted)
• Appearance: /
• Density: 1.315±0.06 g/cm3(Predicted)
• PKA: 11.03±0.60(Predicted)
• CAS DataBase Reference: 4-Oxazolidinecarboxamide, 5-methyl-N-[(1S)-2-[(2R)-2-methyl-1-pyrrolidinyl]-2-oxo-1-(4-thiazolylmethyl)ethyl]-2-oxo-, (4S,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Oxazolidinecarboxamide, 5-methyl-N-[(1S)-2-[(2R)-2-methyl-1-pyrrolidinyl]-2-oxo-1-(4-thiazolylmethyl)ethyl]-2-oxo-, (4S,5S)-(204386-76-5)
• EPA Substance Registry System: 4-Oxazolidinecarboxamide, 5-methyl-N-[(1S)-2-[(2R)-2-methyl-1-pyrrolidinyl]-2-oxo-1-(4-thiazolylmethyl)ethyl]-2-oxo-, (4S,5S)-(204386-76-5)

Safety Data

• Hazardous Substances Data: 204386-76-5(Hazardous Substances Data)

Upstream product

• 85995-53-5 (2S,3S)-2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoic acid 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 98302-45-5 (4S,5S)-5-methyl-2-oxooxazolidine-4-carboxylic acid 
• 765-38-8 (R)-(-)-2-methylpyrrolidine 
• 204387-55-3 (R)-(+)-2-methylpyrrolidine p-toluenesulfonate 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 157007-54-0 2-(R)-methylpyrrolidine-1-carboxylic acid tert-butyl ester 
• 204387-38-2 (2S)-2-amino-3-(thiazol-4-yl)propanoic acid p-toluenesulfonate 
• 119433-80-6 (2S)-2-amino-3-(thiazol-4-yl)propanoic acid 
• 204387-40-6 benzhydryl (2S)-2-amino-3-(thiazol-4-yl)propanoate p-toluenesulfonate 

Relevant articles and documents

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.