192060-67-6

Basic information

• Product Name: Propanamide, N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl-
• Synonyms: N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methylpropionamide;N-((1R,2R)-1-Hydroxy-1-phenylpropan-2-yl)-N-methylpropionamide;(1R,2R)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methylpropionic amide;Propanamide,N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl;(R,R)-N-(2-hydroxy-1-methyl-2-phenethyl)-N-methylpropionamide;(1R,2R)-(-)-Pseudoephedrinepropionamide;(1R,2R)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methylpropionamide;(R,R)-N-(2-hydroxy-1-methyl-2-phenylethyl)-N-methyl propionamide
• CAS NO: 192060-67-6
• Molecular Formula: C13H19NO2
• Molecular Weight: 221.299
• Mol File: 192060-67-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 374.1±35.0 °C(Predicted)
• Density: 1.065±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Propanamide, N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanamide, N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl-(192060-67-6)
• EPA Substance Registry System: Propanamide, N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N-methyl-(192060-67-6)

Safety Data

• Hazardous Substances Data: 192060-67-6(Hazardous Substances Data)

Upstream product

• 321-97-1 (1R,2R)-pseudoephedrine 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 

Downstream Products

• 249745-72-0 (2S)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylhexanamide 
• 249745-85-5 (2S,4S)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethyloctanamide 
• 252569-89-4 (2S,4S)-4-benzyloxy-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2-dimethylpentanamide 
• 333718-31-3 (2S,6S)-N-[(1R,2R)-N-(2-hydroxy-1-methyl-2-phenyl)ethyl]-N,2,6-trimethyloctanamide 
• 192060-69-8 (1'R,2'R,S)-N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N,2-dimethyl-4-[(triisopropylsilyl)oxy]butanamide 
• 618448-72-9 [1R,2R(S)]-N-(2-hydroxy-1-methyl-2-phenylethyl)-N,2-dimethylpentionamide 
• 754239-25-3 (1'R,2'R,2S,4S)-5-benzyloxy-2,4-dimethylpentanoic acid (2'-hydroxy-1'-methyl-2'-phenylethyl)methylamide 
• 865668-35-5 (2R,4R)-7-((tert-butyldimethylsilyl)oxy)-4-hydroxy-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylheptanamide 
• 922523-34-0 (2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-methyl-amide 
• 1030594-77-4 (2S,4R,5R)-5-(tert-butyldimethylsilyloxy)-N-[(1R,2R)-2-hydroxy-1-methyl-2-phenylethyl]-N,2,4-trimethylhept-6-enamide 
• 1001208-19-0 (2S,4R)-5-(tert-butyldiphenylsilyloxy)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2,4-trimethylpentanamide 
• 1132969-88-0 (S,E)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-5-iodo-N,2,4-trimethylpent-4-enamide 
• 1163245-33-7 C₃₁H₄₁NO₃Si 
• 681830-15-9 (1R,2R)-N-[(2R,4R)-4-hydroxy-2-methyl]pentanoylpseudoephedrine 

Relevant articles and documents

Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp: Urolepis rufipes

Males of the parasitoid wasp Urolepis rufipes use 2,6-dimethyl-7-octene-1,6-diol as a sex pheromone to attract virgin females. Herein, we determine the absolute configuration of the pheromone to be (2S,6S)-2,6-dimethyl-7-octene-1,6-diol (2S,6S-6) and present a stereoselective synthesis of the natural enantiomer of this new linalool derivative. In addition, we show that female wasps respond to the natural 2S,6S-6 stereoisomer while 2R,6S-6 is behaviorally inactive.

Structure-Elucidating Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone C §

The (polyenoyl)tetramic acid militarinone C (1) heads a family of seven members. Before our work, the configuration of C-5 was unknown whereas the configurations of C-8′ and C-10′ were either (R,R) or (S,S). We synthesized the four stereoisomers of constitution 1, which conform with these insights. This included cross-coupling both enantiomers of the western building block (8) with both enantiomers of the eastern building block (9). The specific rotations of the resulting 1 isomers suggested that natural 1 is configured like the coupling partners (S)-8 and (R,R)-9. This conclusion was corroborated by degrading natural 1 to alcohol 35 and by proving its configurational identity with synthetic (R,R)-35.

METHODS FOR PRODUCING BERAPROST AND ITS DERIVATIVES

The present invention is directed to methods for preparing Beraprost and novel synthetic intermediates for Beraprost. In one aspect, a process is provided to produce a pharmaceutical compound represented by the general Formula (I) via a radical cyclization route. The process is completed in fewer steps than the known synthetic methods and may be conducted to prepare commercially useful quantities. In another aspect, synthetic methods are provided for producing Beraprost and its derivatives,, which are stereoselective, efficient, scalable and economical. In another aspect, substantially isomerically pure compounds and intermediates are produced by the above processes.