198273-23-3

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 19810-31-2 Benzyloxyacetyl chloride 
• 911411-42-2 (1S)-1-phenyl-N-[(E)-2,2,2-trifluoroethylidene]ethanamine 

Downstream Products

• 198273-25-5 (2R,3R)-methyl 2-(benzyloxy)-4,4,4-trifluoro-3-((S)-1-phenylethyl-amino)butanoate 

Relevant academic research and scientific papers

SUBSTITUTED SULFONAMIDOPROPIONAMIDES AND METHODS OF USE

This invention is in the field of pharmaceutical agents and specifically relates to compounds, compositions, uses and methods for treating inflammation-related disorders, including pain.

Diastereoselective Synthesis of the Nonracemic Methyl syn-(3-Fluoroalkyl)isoserinates

Cycloaddition of the (fluoroalkyl)imines 7a-c with the ketene formed in situ from (benzyloxy)acetyl chloride and triethylamine provided stereoselectively cis-(fluoroalkyl)azetidinones 5a-c in moderate yields. The corresponding N-Boc-isoserinates 11a-c and protected synthons 12a-c have been prepared from these azetidinones 5a-c. Cycloaddition of the chiral imine 18 (RF = CF3) with the same ketene led to the diastereoisomeric azetidinones 19 and 20 with a poor diastereoisomeric excess (10-20%) However, the two diastereoisomers could be easily separated by crystallization and provided enantiomerically pure N-Boc-isoserinates 23 (R,R) and 23 (S,S) after ring opening and debenzylation.