220887-32-1

Basic information

• Product Name: 5-Amino-2-[bis-(phenylmethyl)-amino]-1,6-diphenyl-4-hexen-3-one
• CAS NO: 220887-32-1
• Molecular Weight: 460.619
• Mol File: 220887-32-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5-Amino-2-[bis-(phenylmethyl)-amino]-1,6-diphenyl-4-hexen-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-2-[bis-(phenylmethyl)-amino]-1,6-diphenyl-4-hexen-3-one(220887-32-1)
• EPA Substance Registry System: 5-Amino-2-[bis-(phenylmethyl)-amino]-1,6-diphenyl-4-hexen-3-one(220887-32-1)

Safety Data

• Hazardous Substances Data: 220887-32-1(Hazardous Substances Data)

Upstream product

• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 
• 75-05-8 acetonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 100-44-7 benzyl chloride 
• 156732-12-6 (4S)-4-(N,N-dibenzylamino)-3-oxo-5-phenyl-pentanonitrile 
• 63-91-2 L-phenylalanine 

Downstream Products

• 156732-15-9 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane 

Relevant articles and documents

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.

Novel Lopinavir analogues incorporating non-Aromatic P-1 side chains - Synthesis and structure-activity relationships

The HIV protease inhibitor Lopinavir has a pseudosymmetric core unit incorporating benzyl groups at both P-1, P-1′ positions. A series of analogues incorporating non-aromatic side chains at the P-1 position were synthesized and the structure-activity relationships explored.

A convenient synthesis of enaminones using tandem acetonitrile condensation Grignard addition

Condensations of N,N-dibenzyl α-amino esters with the anion of acetonitrile followed by the addition of a Grignard reagent(proceed in excellent yields. This affords rapid access to the peptidomimetic precursor α-amino enaminones in one pot one the esters.