170801-80-6

Basic information

• Product Name: (R)-(+)-N-(3,3-Diethoxypropyl)-3-(3,4-dimethoxyphenyl)-2-hydroxypropionamide
• Synonyms: (R)-(+)-N-(3,3-Diethoxypropyl)-3-(3,4-dimethoxyphenyl)-2-hydroxypropionamide
• CAS NO: 170801-80-6
• Molecular Weight: 355.431
• Mol File: 170801-80-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-(+)-N-(3,3-Diethoxypropyl)-3-(3,4-dimethoxyphenyl)-2-hydroxypropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-N-(3,3-Diethoxypropyl)-3-(3,4-dimethoxyphenyl)-2-hydroxypropionamide(170801-80-6)
• EPA Substance Registry System: (R)-(+)-N-(3,3-Diethoxypropyl)-3-(3,4-dimethoxyphenyl)-2-hydroxypropionamide(170801-80-6)

Safety Data

• Hazardous Substances Data: 170801-80-6(Hazardous Substances Data)

Upstream product

• 41365-75-7 aminopropane diethyl acetal 
• 54814-41-4 3-(3,4-dimethoxy-phenyl)-2-hydroxy-propionic acid methyl ester 
• 170801-78-2 Methyl (R)-(+)-2-benzoyloxy-3-(3,4-dimethoxyphenyl)propionate 
• 2032-34-0 3,3-bis(ethyloxy)propanenitrile 
• 153381-08-9 Methyl (S)-(+)-3-(3,4 dimethoxyphenyl)-2-hydroxypropionate 

Relevant articles and documents

Tricyclic CNS active agents by intramolecular Oxa-Pictet-Spengler reaction

Mitsunobu inversion of the (S)-configurated lactate (S)-7, which is prepared in four steps starting from (S)-tyrosine, leads to the (R)-configurated lactate (R)-7. The key step in the transformation of the enantiomeric lactates (S)-7 and (R)-7 into the benzomorphan analogous tricycles (R,S)-16a,b, (S,R)-16a,b, (S,S)-22, and (R,R)-22 is an intramolecular Oxa-Rictet-Spengler reaction: The amides (S)-13, (R)-13, (S)-19 and (R)-19, in which the carbonyl moiety - masked as an acetal - is linked to the 2-phenylethanol moiety, are cyclized to give the tricyclic amides (R,S)-15, (S,R)-15, (S,S)-21, and (R,R)-21, respectively. In a concentration of 100 μM both enantiomers of 16a, 16b, and 22 are not able to compete with 3H-(+)-MK 801 for the phencyclidine binding sites of NMDA receptors. In vivo, only (R,S)-16b and (S,S)-22 exhibit weak sedative and analgesic activity.