64528-62-7

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 3282-30-2 pivaloyl chloride 
• 64528-63-8 N-(1-phenylethyl)pivalamide 
• 109801-89-0 2,2-Dimethyl-propionic acid (S)-1-(2,2-dimethyl-propionyloxycarbonyl)-2-methyl-propyl ester 
• 75-98-9 Trimethylacetic acid 

Downstream Products

• 183204-12-8 2,2-Dimethyl-N-{(S)-1-[2-(2-oxo-2-phenyl-ethanesulfonyl)-phenyl]-ethyl}-propionamide 

Relevant academic research and scientific papers

Methyltrimethoxysilane (MTM) as a Reagent for Direct Amidation of Carboxylic Acids

Methyltrimethoxysilane [MTM, CH3Si(OMe)3] has been demonstrated to be an effective, inexpensive, and safe reagent for the direct amidation of carboxylic acids with amines. Two simple workup procedures that provide the pure amide product without the need for further purification have been developed. The first employs an aqueous base-mediated annihilation of MTM. The second involves simple product crystallization from the reaction mixture providing a low process mass intensity direct amidation protocol.

Efficient Synthesis of Sulfinate Esters and Sulfinamides via Activated Esters of p -Toluenesulfinic Acid

Sulfinate esters were prepared by the process of activating p -toluenesulfinic acid with either cyanuric chloride, methanesulfonyl chloride, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl). Activation of p -toluenesulfinic acid with cyanuric chloride led to the formation of sulfinate esters that were accompanied by the formation of the corresponding sulfones. The use of methanesulfonyl chloride for activation via methanesulfonic p -toluenesulfinic anhydride afforded mixtures of sulfinate esters and methanesulfonates. The use of the carbodiimide EDC proved to yield the best results with the highly selective formation of the target sulfinate esters. The use of trimethylacetic p -toluenesulfinic anhydride or cyanuric chloride to achieve the synthesis of sulfinamides proved to be ineffective due to poor chemoselectivity of the nucleophilic attack on the activated p -toluenesulfinic acid anhydride. Ultimately, the use of EDC-HCl to form the sulfinamides proved to be the best pathway for synthesis.

Enantiopure Amidinate Complexes of the Rare-Earth Elements

The synthesis of the new chiral amidine (S,S)-N,N′-bis(1-phenylethyl)pivalamidine ((S)-HPETA) and its corresponding lithium salt (S)-LiPETA are reported, and their solid-state structures were investigated by single-crystal X-ray diffraction. Depending on the stoichiometric ratio and the ion radius of the rare-earth metal, the reaction of (S)-LiPETA with anhydrous lanthanide trihalides (Ln = Sc, Y, La, Nd, Sm, Lu) afforded mono-, bis-, and tris(amidinate) complexes. The mono(amidinate) compound [{(S)-PETA}LaI4Li2(thf)4], the bis(amidinate) complexes [({(S)-PETA}2Ln-μ-Cl)n] (Ln = Sc, Y, Nd, Sm, Lu), and the tris(amidinate) compound [{(S)-PETA}3Y] were isolated and structurally characterized by single-crystal X-ray diffraction. For the bis(amidinate) compounds, either monomeric or chloro-bridged dimeric structures were observed in the solid state. Furthermore, chiral bis(amidinate)-amido and -alkyl complexes [{(S)-PETA}2Ln{E(SiMe3)2}] (E = N, Ln = Y; E = CH, Ln = Sc, Y, Lu) were synthesized by salt metathesis and their catalytic activity and enantioselectivities were investigated in hydroamination/cyclization reactions. All of these compounds showed very good catalytic activity, and all of the investigated substrates were converted regiospecifically into their corresponding cyclic products under mild reaction conditions within good reaction times. The lutetium alkyl compound combined a high activity with good enantioselectivity.

A Versatile and practical solvating agent for enantioselective recognition and NMR analysis of protected amines

The 3,5-dinitrobenzoyl-derived 1-naphthylethyl amide 3 is an attractive CSA for NMR analysis of protected amines. It is readily prepared in a single step and combines practical resolution of diastereomeric complexes due to signal sharpness and effective signal separation. Crystallographic analysis shows that 3 forms a chiral cleft that can selectively bind one enantiomer of a substrate through hydrogen bonding, π-π stacking, and CH/π interactions. The enantioselective complex formation causes strong upfield shifts in the 1H NMR spectrum even in the presence of only 5 mol % of 3.

Synthesis of a substituted benzazepin-2-one dihydrate

Synthesis of the title compound was accomplished via coupling of (S)-alaninyl-(S)-1-amino-3-methyl-4,5,6,7-tetrahydro-2H-3-benzazepin-2-one with the activated trimethylsilyl ester of (S)-2-trimethylsilyloxy-3-methylbutyric acid, followed by deprotection a

NEW CHIRAL STATIONARY PHASES FOR CHROMATOGRAPHY BASED ON AROMATIC ALLYL AMINES

New chiral stationary phases (CSPs) based on chiral selectors covalently bound on a solid support were prepared. Chiral selectors were obtained from enantiomerically pure aromatic amines and 3,5-dinitrobenzoic acid and then linked to the support surface through the allylic double bond. Such obtained materials allow enantioseparation of racemates or enantiomerically enriched compounds. These chiral stationary phases can be used as fillings in chromatographic columns for enantiomer separation of naproxen type drugs and other similar non-steroidal anti-inflammatory drugs (NSAID) by means of high performance liquid chromatography on both the analytical and preparative scale.

Alternative and complementary approaches to the asymmetric synthesis of C3 substituted NH free or N-substituted isoindolin-1-ones

Complementary synthetic approaches to enantiomerically pure C3 alkylated or arylated NH free or N-substituted isoindolinones have been developed. The key step is elaboration of diversely substituted 2-alkyl- and arylbenzylamines, which can be submitted to a bis-metallation process followed by interception with a carbonylating agent. They can be also converted into N-alkylbromobenzylcarbamates or into bromobenzyldicarbamates and the assembly of the titled compounds can be readily ensured by reliance upon the Parham cyclization process.

4-Phenyloxazolidin-2-ones and isoindolin-1-ones: Chiral auxiliaries for Diels-Alder reactions of N-substituted 1,3-dienes

Terminally N-substituted dienes derived from 3-methylisoindolin-1-one, 4-isopropyl- and 4-phenyloxazolidin-2-one undergo Diels-Alder reaction with a range of activated dienophiles. The reactions reported are completely regio- and endo-selective, with the diastereoisomeric excess with respect to the auxiliary good to excellent in most of the cases reported. A model has been developed for rationalising the stereochemical outcome of these reactions.

Asymmetric synthesis of β-hydroxy sulfones by reduction of chiral β-keto sulfones

Chiral β-keto sulfones 3 have been prepared from enantiomerically pure sulfinic acids 2 derived from (R)- and (S)-methylbenzylamine. Enantiospecific reduction of these ketosulfones 3 can be achieved using different hydrides affording β-hydroxy sulfones. O