92235-33-1

Upstream product

• 135339-65-0 N^α,N,N-tris(tert-butoxycarbonyl)-(S)-prolinamide 
• 100-46-9 benzylamine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 141874-26-2 N-Boc-(S)-proline chloride 
• 7531-52-4 L-prolinamide 
• 541-35-5 butanamide 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 35150-07-3 (S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate 
• 135097-23-3 (2S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 147-85-3 L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 914097-64-6 tert-butyl (2S)-2-(benzylthiocarbamoyl)pyrrolidine-1-carboxylate 
• 75773-76-1 (S)‐N‐benzyl‐1‐(pyrrolidin‐2‐yl) methanamine 
• 1281987-89-0 C₁₆H₂₄N₂O₂S 
• 1236255-21-2 L-proline benzylamide hydrochloride 
• 904326-08-5 (2S)-N-benzylpyrrolidine-2-carbothioamide 
• 116774-46-0 (S)-N-Benzylpyrrolidine-2-carboxyamide 

Relevant academic research and scientific papers

Synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid

The invention relates to a synthetic method for preparing amide compounds through co-catalysis of niobium pentachloride and ionic liquid. The preparation method is characterized by comprising the following steps: weighing organic carboxylic acid, organic amine, niobium pentachloride, ionic liquid and a molecular sieve, adding the materials into a reactor, adding an organic solvent, and reacting for 6-24 hours at the reaction temperature of 70-110 DEG C to obtain a corresponding amide product. The molar ratio of the organic carboxylic acid to the organic amine to the niobium pentachloride to the ionic liquid is 1:(1-3):(0.01-1):(0.05-1); wherein the mass ratio of the organic carboxylic acid to the molecular sieve is 1: (0.2-1). According to the method, the substrate range is expanded, the reaction yield is high (95% or above), the catalyst dosage is small, the atom economy is high, the catalyst is cheap and easy to obtain, the production cost can be greatly reduced, and the method is suitable for industrial production.

Direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2

This paper described a mild and efficient direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good to excellent yield. Chiral amino acids derivatives were transformed into amides without racemization in moderate yield. The possible mechanism of direct amidation catalyzed by TiCp2Cl2 was discussed. This catalytic method is very suitable for the amidation of low sterically hindered arylacetic acid, fatty acids with different low sterically hindered amines except aniline, as well as the amidation of aryl formic acid with benzyl and aliphatic amines.

Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides

Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.

Tetramethyl Orthosilicate (TMOS) as a Reagent for Direct Amidation of Carboxylic Acids

Tetramethyl orthosilicate (TMOS) is shown to be an effective reagent for direct amidation of aliphatic and aromatic carboxylic acids with amines and anilines. The amide products are obtained in good to quantitative yields in pure form directly after workup without the need for any further purification. A silyl ester as the putative activated intermediate is observed by NMR methods. Amidations on a 1 mol scale are demonstrated with a favorable process mass intensity.

Synthesis and antitumor activities of chiral dipeptide thioureas containing an alpha-aminophosphonate moiety

Thiourea derivatives demonstrate potent cytotoxic activity against various leukemias and many tumor cell lines. In our previous study, the combination of thiourea and phosphonate has been proven as an effective strategy for developing antitumor agents. Herein, we synthesized and evaluated a series of novel chiral dipeptide thioureas containing an α-aminophosphonate moiety as antitumor agents. Finally, we developed novel dipeptide thioureas 11d and 11f that showed comparable inhibition with that of Cisplatin against BGC-823 and A-549 cells, respectively.

[...] - Orn (ClCH2NH) - AA - benzylamine, its synthesis, activity and application (by machine translation)

The invention discloses the following formula of 13 for β - Carboline -3 - formyl - Orn (ClCH2 NH) - AA - NHCH2 C6 H5 (In the formula AA is selected from L - Arg, L - Asn, L - Asp, L - Glu, L - Gly, L - Ile, L - Leu, L - Met, L - Phe, L - Pro, L - Thr, L - Trp, L - Val residue), discloses a process for their preparation, discloses their inhibition of tumor cell growth, therefore this invention discloses their use as anti-tumor medicament. (by machine translation)

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

Nickel-Catalyzed Esterification of Aliphatic Amides

Recent studies have demonstrated that amides can be used in nickel-catalyzed reactions that lead to cleavage of the amide C?N bond, with formation of a C?C or C?heteroatom bond. However, the general scope of these methodologies has been restricted to amides where the carbonyl is directly attached to an arene or heteroarene. We now report the nickel-catalyzed esterification of amides derived from aliphatic carboxylic acids. The transformation requires only a slight excess of the alcohol nucleophile and is tolerant of heterocycles, substrates with epimerizable stereocenters, and sterically congested coupling partners. Moreover, a series of amide competition experiments establish selectivity principles that will aid future synthetic design. These studies overcome a critical limitation of current Ni-catalyzed amide couplings and are expected to further stimulate the use of amides as synthetic building blocks in C?N bond cleavage processes.

Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis

An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.