156732-12-6

Basic information

• Product Name: 4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile
• Synonyms: 4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile;(S)-4-N,N-DIBENZYLAMINO-3-OXO-5-PHENYL-PENTANONITRILE;(4S)-4-(N,N-DibenzylaMino)-5-phenyl-3-oxopentanenitrile;4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanenitrile
• CAS NO: 156732-12-6
• Molecular Formula: C₂₅H₂₄N₂O
• Molecular Weight: 368.47
• Product Categories: Aromatics;Chiral Reagents;Intermediates
• Mol File: 156732-12-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 510.0±50.0 °C(Predicted)
• Appearance: /
• Density: 1.136±0.06 g/cm3(Predicted)
• PKA: 8.71±0.10(Predicted)
• CAS DataBase Reference: 4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile(156732-12-6)
• EPA Substance Registry System: 4-S-N,N-Dibenzylamino-3-oxo-5-phenyl-pentanonitrile(156732-12-6)

Safety Data

• Hazardous Substances Data: 156732-12-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An intermediate in the synthesis of Ritonavir.

Upstream product

• 63-91-2 L-phenylalanine 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 75-05-8 acetonitrile 

Downstream Products

• 220887-32-1 (5S)-2-Amino-5-(N,N-dibenzylamino)-4-oxo-1,6-diphenylhex-2-ene 
• 156732-13-7 (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene 
• 330457-56-2 (S)-2-amino-N-[(2S,4S,5S)-5-(dibenzylamino)-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methylbutanamide 
• 156732-15-9 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane 

Relevant articles and documents

Superior chiral retention with lithium amide in cyanomethylation of N,N- dibenzyl L-phenylalanine benzyl ester

Lithium amide is shown to give better retention of chirality over sodium amide in the nucleophilic addition of acetonitrile to N,N-dibenzyl L- phenylalanine benzyl ester. Solvent effect is obvious in the case of sodium amide.

Method for synthesizing ritonavir intermediate

The invention relates to a method for synthesizing a ritonavir intermediate. The intermediate is (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. The method comprises the following steps: mixing L-phenylalanine, water and sodium hydroxide, adding benzyl chloride, adding heptane, washing the above obtained material with a methanol-water solution, and carrying out reduced pressure evaporation to obtain yellow oil benzyl 2-dibenzylamino-3-phenylpropionate; and dissolving the yellow oil in methyl tert-butyl ether under the protection of nitrogen, reacting the obtained solution with anhydrous acetonitrile, adding sodium hydride, stirring all above materials, slowly dropwise adding a Grignard reagent, cooling, adding anhydrous methanol for hydrolyzing superfluous sodium amide, allowing the obtained solution to stand for layering, extracting the obtained water layer with methyl tert-butyl ether, mixing oil layers, concentrating the obtained oil layer mixture, evaporating the obtained concentrate to obtain oil, adding anhydrous methanol, filtering the oil, and carrying out vacuum drying to obtain white powder which is the ritonavir intermediate (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one. Compared with traditional technologies, the method provided by the invention has the advantages of reaction step simplification, reaction cost reduction, and reduction of use of toxic reagents.

Aspartic protease inhibitors

The present invention provides a compound of formula (I) wherein a, b, c, d, and e, are R7, OR7, SR7, NR7R8, NHCOR7, CO2R7, CN, NO2, NH2, N3, or a halogen. R7and R8are H or alkyl, R1and R2are H or alkyl, and R3is a non-aromatic substituent. Substituent A is OH, NH2, or SH. Substituents B and B1include amide and sulfonamide groups, which can be cyclic, acyclic, or amino acid derivatives. Alternatively, B and R′ together with the nitrogen to which they are bonded, and/or B′ and R2together with the nitrogen to which they are bonded, define a heterocycle. The present invention further provides a pharmaceutical composition that includes a carrier and a therapeutically effective amount of at least one compound of the present invention. The present invention further provides therapeutic methods that include administering a therapeutically effective amount of at least one compound of the present invention