17451-66-0

Basic information

• Product Name: N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine
• Synonyms: N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine
• CAS NO: 17451-66-0
• Molecular Weight: 340.292
• Mol File: 17451-66-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine(17451-66-0)
• EPA Substance Registry System: N-phthaloyl-3-(4-nitrophenyl)-(S)-alanine(17451-66-0)

Safety Data

• Hazardous Substances Data: 17451-66-0(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 207569-25-3 p-nitro-L-phenylalanine hydrate 
• 100-14-1 4-nitrobenzyl chloride 
• 855633-22-6 (4-nitro-benzyl)-phthalimido-malonic acid diethyl ester 
• 101445-16-3 N-(2-carboxy-benzoyl)-4-nitro-phenylalanine 
• 60666-01-5 (RS)-N-phthaloyl-p-nitrophenylalanine 
• 22509-74-6 N-ethoxycarbonylphthalimide 

Downstream Products

• 17451-67-1 N-phthalimido-4-nitro-L-phenylalanine ethyl ester 
• 1290176-64-5 (2S)-2-methyl-1-[3-(4-nitrophenyl)-N-phthaloyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline 
• 97338-02-8 N-phthalimido-4-(bis-2-hydroxyethyl)amino-L-phenylalanine ethyl ester 
• 74743-23-0 N-phthalimido-4-amino-L-phenylalanine ethyl ester 
• 178601-78-0 (2S,3R)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-nitro-phenyl)-propionamide 
• 175476-28-5 (S)-N-tert-Butyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-nitro-phenyl)-propionamide 
• 129446-45-3 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid 

Relevant articles and documents

Synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester

The invention provides a synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester. The process includes the first step of amino protection reaction, the second step of esterification reaction, the third step of reduction reaction and the fourth step of substitution reaction. According to the synthesis process, amino is protected by phthalic anhydride, and then esterification, reduction and substitution are conducted obtain the product. The process has the advantages of being low in cost, mild in reaction condition, low in toxicity, convenient to operate, high in yield and suitable for industrial production.

Neighbouring group effects promote substitution reactions over elimination and provide a stereocontrolled route to chloramphenicol

In reactions of β-brominated valine and p-nitrophenylalanine derivatives to give β-hydroxy amino acid derivatives the carboxyl group, when protected as an amide, exerts a neighbouring group effect to facilitate the substitution process, and reduce competing elimination reactions. As a consequence of the effect, the (2R,3R)- and (2R,3S)-stereoisomers of 3-bromo-N-tert-butyl-N(α)-phthaloyl-p-nitrophenylalaninamide both react to give (2S,3R)-3-hydroxy-N-tert-butyl-N(α)-phthaloyl-p-nitrophenylalaninamid e, providing a stereoconvergent route to chloramphenicol.