216319-90-3

Usage

Uses

Used in Organic Chemistry:
Boc-L-Val-nitrile is used as a building block for the synthesis of complex organic compounds, leveraging its Boc protecting group and nitrile functional group to enable selective reactions and further modifications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Boc-L-Val-nitrile is utilized as a key component in the development of peptide-based drugs. Its Boc group allows for controlled synthesis of peptide sequences, while the nitrile group offers a point of attachment for additional functional groups, enhancing the compound's therapeutic potential.
Used in Peptide Synthesis:
Boc-L-Val-nitrile is employed as a crucial intermediate in peptide synthesis, where its Boc protecting group ensures that the leucine amino acid's reactive sites are selectively engaged during the assembly of peptide chains. The nitrile group also serves as a versatile handle for post-synthetic modifications, broadening the scope of possible peptide structures and functions.
Used in Drug Development:
Boc-L-Val-nitrile is used as a precursor in the design and synthesis of innovative drugs, particularly in the realm of peptide therapeutics. Its unique structural features facilitate the creation of bioactive molecules with tailored properties, such as enhanced stability, selectivity, and bioavailability, ultimately contributing to the advancement of new treatment options for various diseases and conditions.

InChI:InChI=1/C10H18N2O2/c1-7(2)8(6-11)12-9(13)14-10(3,4)5/h7-8H,1-5H3,(H,12,13)/t8-/m1/s1

Upstream product

• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 271600-32-9 [2-methyl-1-(toluene-4-sulfonyl)-propyl]-carbamic acid tert-butyl ester 
• 35150-08-4 Boc-Val-NH₂ 
• 13734-41-3 t-Boc-L-valine 
• 72-18-4 L-valine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98807-40-0 Boc-Val-O-COOEt 

Downstream Products

• 400652-49-5 (2S)-N²-(tert-butoxycarbonyl)-3-methyl-1,2-butanediamine 

Relevant academic research and scientific papers

Design, synthesis and cytotoxic evaluation of a library of oxadiazole-containing hybrids

The development of hybrid compounds led to the discovery of new pharmacologically active agents for some of the most critical diseases, including cancer. Herein, we describe a new series of oxadiazole-containing structures designed by a molecular hybridiz

Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation

The preparation of nitriles from primary amides or aldoximes was achieved by using oxalyl chloride with a catalytic amount of dimethyl sulfoxide in the presence of Et3N. The reactions were complete within 1 h after addition at room temperature. A diverse range of cyano compounds were obtained in good to excellent yields, including aromatic, heteroaromatic, cyclic, and acyclic aliphatic species.

One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones

A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.

Isoselenocyanates derived from Boc/Z-amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The 1H NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenoureido derivatives is free from racemization.

Synthesis of Boc-amino tetrazoles derived from α-amino acids

A simple route for the synthesis of Boc-protected tetrazole analogs of amino acids starting from Nα-Boc amino acids has been described. The [2 + 3] cycloaddition of Boc-α-amino nitrile and sodium azide in the presence of a catalytic amount of zinc bromide yielded the desired tetrazoles in good yields and purity. All the compounds obtained have been characterized by 1H and 13C-NMR and mass spectral studies. Copyright Taylor & Francis Group, LLC.

The preparation of optically active α-amino 4H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids

Optically active α-amino 4H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described.

N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides

(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.

Design and synthesis of dipeptidyl nitriles as potent, selective, and reversible inhibitors of cathepsin C

A series of dipeptide nitriles with a thienyl alanine in P2 were identified as potent and selective cathepsin C inhibitors. Incorporation of a substituted cyclopropyl moiety in P1 effectively protects these derivatives against hydrolase activity in whole blood.

Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles as peptidomimetic building blocks

Twelve new 1,2,4-oxadiazole based compounds have been synthesized. Their structures contain a protected amine and a carboxyl or an ester group, and thus serve as potential peptidomimetic building blocks. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained.

Phase transfer catalyzed enantioselective strecker reactions of α-amido sulfones with cyanohydrins

A study into the use of a chiral phase-transfer catalyst in conjunction with acetone cyanohydrin to effect the enantioselective formation of α-amino nitriles from α-amido sulfones is described. This novel catalytic asymmetric Strecker reaction is analyzed