114877-91-7

Usage

InChI:InChI=1/C7H11NO2S/c1-5(2)6(8-4-11)7(9)10-3/h5-6H,1-3H3

Upstream product

• 75-15-0 carbon disulfide 
• 5619-05-6 DL-valine methyl ester hydrochloride 
• 463-71-8 thiophosgene 
• 6306-52-1 L-valine methylester hydrochloride 
• 72-18-4 L-valine 
• 4070-48-8 L-Valine methyl ester 

Downstream Products

• 114877-93-9 (S)-1-(diphenylphosphino)-N-(1-(methoxycarbonyl)-2-methylpropyl)thioformamide 
• 1246168-81-9 C₂₀H₃₀N₄O₅S₂ 
• 1246168-74-0 Boc-Phe-NH-NH-CS-Val-OMe 

Relevant academic research and scientific papers

Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent

Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.

Co-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters

An efficient radical transannulation reaction of pyridotriazoles with isothiocyanates and xanthate esters was developed. This method features conversion of pyridotriazoles into two N-fused heterocyclic aromatic systems-imino-thiazolopyridines and oxo-thia

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

Chiral recognition of carboxylates by a static library of thiourea receptors with amino acid arms

Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and α-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

A facile one-pot synthesis of selenoureidopeptides employing lialhseh through staudinger aza-wittig-type reaction

A one-pot protocol for the synthesis of selenoureidopeptides employing lithium aluminum hydride hydroselenide (LiAlHSeH) as a selenating agent via a Staudinger aza-Wittig-type reaction is reported. The protocol involves the use of Nα-protected aminoalkyl azides and isothicyanato esters to afford the desired products in good yields. This protocol is a direct approach to the synthesis of selenourea compounds that avoids the synthesis of isoselenocyanates and does not require multistep synthesis.

A facile synthesis of N-Z/Boc-protected 1,3,4-oxadiazole-based peptidomimetics employing peptidyl thiosemicarbazides

Synthesis of 1,3,4-oxadiazole containing peptidomimetics is described by a p-TsCl/pyridine-mediated cyclization of the corresponding dipeptidyl thiosemicarbazides, which are readily prepared by coupling N-protected amino acid hydrazides with amino acid-derived isothiocyanato esters. Further, the protocol has also been extended for the synthesis of orthogonally protected 1,3,4-oxadiazole tethered mimetics as well. The synthetic route is simple and mild conditions are used so that the chirality of the starting amino acids is retained.

Novel derivatives of benzimidazole and imidazo-pyridine and their use as medicaments

A compound of the formula wherein the substituents are as defined in the specification and pharmaceutical salts thereof having a good affinity for sub-types of melanocortin receptors making them useful for treating diseases in which such receptors are included such as pain, inflammatory conditions, etc.

SYNTHESIS OF CHIRAL THIOCARBAMOYLPHOSPHINES DERIVED FROM AMINO ACIDS

The methylester hydrochlorides of the (S)-amino acids L-alanine (1a), L-phenylalanine (1b), L-valine (1c) and L-lysine (1d) were converted to the corresponding isothiocyanates 2a-d by thiophosgenation. 2a-d React with secondary phosphines and phosphine oxides to give the thiocarbamoylphosphines 3a-d and P-oxides 4a, b.