199927-20-3

Upstream product

• 72155-45-4 Boc-L-phenylalaninal 
• 199926-80-2 ethyl (S)-(-)-6-(N-tert-butoxycarbonyl)amino-3-ethoxy-7-phenylhepta-2,4-dienoate 
• 145822-68-0 (E)-[2-ethoxy-3-(ethoxycarbonyl)-2-propenylidene]triphenylphosphorane 
• 199926-94-8 ethyl (S)-(-)-6-(N-tert-butoxycarbonyl-N-methyl)amino-3-ethoxy-7-phenylhepta-2,4-dienoate 

Relevant academic research and scientific papers

Synthesis and reaction of chiral 4,5-disubstituted 2-oxazolidinones from 3-ethoxy-6-(N-alkyl-N-tert-butoxy- carbonyl)aminohexa-2,4-dienoates in the presence of concentrated sulfuric acid supported on silica gel

Reaction of chiral 3-ethoxy-6-(N-alkyl-N-tert-butoxycarbonyl)amino-hexa- 2,4-dienoates (3) and related compounds with 97% concentrated sulfuric acid supported on silica gel proceeded stereo- and regio-selectively to yield chiral 4,5-disubstituted N-alkyl-2-oxazolidinones (7). Under the limited conditions, 7 were converted into N-alkyl-2-pyrrolylacetates (8) and 2- oxazolidinone derivatives (12) which may serve as a chiral auxiliary.

Synthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates

N-methyl-2-oxazolidinones (4) are obtained stereo- and regio-selectively when 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates (1) are treated with concentrated sulfuric acid (1.0 equiv.) supported on silicagel in dichloromethane at 0 °C. 4 were shown to be intermediates for the construction of N-methylpyrrole ring. The structure and properties of 4 and related compounds are also described.