573701-30-1

Upstream product

• 27646-78-2 (S)-(+)-2-(N-methylamino)propanol 
• 100-52-7 benzaldehyde 
• 175853-53-9 methyl (2S)-2-[benzyl(methyl)amino]propanoate 
• 31022-10-3 N-benzyl-L-alanine methyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 1161828-90-5 [N(S)]-N-allyl-N-benzyl-N-[(1S)-2-hydroxy-1-methylethyl]-N-methylammonium bromide 
• 1161828-99-4 [N(R)]-N-allyl-N-benzyl-N-[(1S)-2-hydroxy-1-methylethyl]-N-methylammonium bromide 
• 573701-34-5 2-Diazo-3-oxo-butyric acid (S)-2-(benzyl-methyl-amino)-propyl ester 

Relevant academic research and scientific papers

THERAPEUTIC COMPOUNDS

The present invention relates to compounds that are antagonists of the orexin-1 receptor. The compounds have the structural formula (I) defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of diseases or disorders associated with orexin-1 receptor activity.

'N-stereogenic quaternary ammonium salts' from L-amino acids: Synthesis, separation, and absolute configuration

Diastereoisomeric linear and cyclic 'N-chiral quaternary ammonium salts' (QASs) were efficiently synthesized from corresponding L-amino acids in high yields. The diastereoisomers of each pair of 'N-chiral QASs' were successfully separated. The absolute configurations of these QASs were determined predominately by X-ray single-crystal analysis. The 1H-NMR data of 'N-chiral QASs' provided characteristic information on the configuration of the N-chiral center. 'N-Chiral QASs' exemplified by [N(R)]-2a and [N(S)]-2a are stable in protic and aprotic solvents within a broad pH and temperature range.

Stereoselective formation and rearrangement of morpholinium ylides derived from copper carbenoids

Amino diazoacetoacetates 4a-e and 7a,b were prepared from readily available amino alcohols and subjected to copper-catalyzed carbene-transfer reaction. Substrates 4c-e furnished the morpholin-2-ones 5c-e in good yield via the corresponding cyclic ammonium ylides, albeit with poor diastereoselectivity. Substrates 4a,b failed to provide the corresponding morpholinones, perhaps as a result of steric congestion. Cyclic substrates 7a,b underwent conversion to bicyclic morpholinones 8 and 9 in good yield and with moderate to good diastereoselectivity. This result is rationalized via control of the transiently stereogenic ammonium center of the intermediate bicyclic ylides.