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

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

• 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.

Molecular tools that block maturation of the nuclear lamin A and decelerate cancer cell migration

Lamin A contributes to the structure of nuclei in all mammalian cells and plays an important role in cell division and migration. Mature lamin A is derived from a farnesylated precursor protein, known as prelamin A, which undergoes post-translational cleavage catalyzed by the zinc metalloprotease STE24 (ZPMSTE24). Accumulation of farnesylated prelamin A in the nuclear envelope compromises cell division, impairs mitosis and induces an increased expression of inflammatory gene products. ZMPSTE24 has been proposed as a potential therapeutic target in oncology. A library of peptidomimetic compounds were synthesized and screened for their ability to induce accumulation of prelamin A in cancer cells and block cell migration in pancreatic ductal adenocarcinoma cells. The results of this study suggest that inhibitors of lamin A maturation may interfere with cell migration, the biological process required for cancer metastasis.

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.

Synthesis of (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one

L-Phenylalanine taken as a starting material is protected with benzyl chloride and procedure simplified by not charging with ethyl alcohol. Subsequently with the further simplification of skipping the atmospheric distillation of MTBE (methyl tert-butyl ether), (S,Z)-5-amino-2-(dibenzylamino)-1,6-diphenylhex-4-en-3-one, the significant intermediate of Ritonavir and Lopinavir, is obtained from cyanidation, Grignard reaction and reduction.

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

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.

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

Process for producing keto nitrile derivative

A process for producing a (4S)-4-(N,N-dibenzyl)amino-5-phenyl-3-oxo-pentanenitrile derivative which comprises reacting a (2S)-2-(N,N-dibenzyl)aminophenylalanine ester derivative with acetonitrile in the presence of a lithium compound or a magnesium compound is disclosed, and a process for producing a (2S)-2-(N,N-dibenzyl)amino-5-amino-1,6-diphenyl-4-hexen-3-one derivative which comprises adding a benzylmagnesium halide or a benzyllithium to a reaction solution containing the (4S)-4-(N,N-dibenzyl)amino-5-phenyl-3-oxo-pentanenitrile derivative and reacting the derivative with the benzylmagnesium halide or the benzyllithium is also disclosed. According to these processes, optically pure (4S)-4-(N,N-dibenzyl)amino-5-phenyl-3-oxo-pentanenitrile derivative and (2S)-2-(N,N-dibenzyl)amino-5-amino-1,6-diphenyl-4-hexen-3-one derivative can be produced in a good yield on an industrial scale.

An Efficient Stereocontrolled Strategy for the Synthesis of Hydroxyethylene Dipeptide Isosteres

A novel and practical synthesis of hydroxyethylene dipeptide isostere 9 from L-phenylalanine via the formation and stereospecific reduction of an enaminone is described.