24268-81-3

Upstream product

• 50-00-0 formaldehyd 
• 150-30-1 Phenylalanine 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 124-40-3 dimethyl amine 
• 67-56-1 methanol 

Downstream Products

• 19881-82-4 (+/-)-N,N-dimethylphenylalanine ethyl ester 
• 135432-32-5 2-Dimethylamino-3-phenyl-propionic acid isopropyl ester 
• 135432-33-6 DL-N-ethoxycarbonyl-N-methylphenylalanine isopropyl ester 
• 64874-83-5 2-(2,2,3,3,3-Pentafluoro-propionylamino)-3-phenyl-propionic acid isopropyl ester 
• 60577-28-8 (+/-)-2-dimethylamino-3-phenyl-propan-1-ol 
• 19881-91-5 (1-benzyl-2-hydroxy-ethyl)-trimethyl-ammonium; iodide 
• 54114-12-4 (1-benzyl-2-hydroxy-ethyl)-trimethyl-ammonium; chloride 
• 1033692-08-8 N-[4-(cyclopropyl-ethyl-amino)-benzyl]-2-dimethylamino-N-(4-fluoro-phenyl)-3-phenyl-propionamide 
• 17469-89-5 (2S)-2-(dimethylamino)-3-phenylpropanoic acid 
• 174222-78-7 (R)-2-(dimethylamino)-3-phenylpropanoic acid 

Relevant academic research and scientific papers

Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions

We report a mild and environmentally benign method for the synthesis of tertiary amines using alcohols as the alkylating reagents. Not only secondary amines such as piperazines but also amino acids and amino alcohols can be N-alkylated selectively. For N,O-benzyl protected amino alcohols, both N,O-de-benzylation and N-methylation were achieved in one-pot. The Royal Society of Chemistry.

Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies

The efficient resolution of racemic N-benzyl α-amino acids (N-Bn-AA) has been achieved by a liquid-liquid extraction process using the lipophilic chiral salen-cobalt(III) complex [CoIII(3)(OAc)]. As a result of the resolution by extraction, one enantiomer (S) of the N-benzyl α-amino acid predominated in the aqueous phase, while the other enantiomer (R) was driven into the organic phase by complexation to cobalt. The complexed amino acid (R) was then quantitatively released by a reductive (CoIII→Co II) counter-extraction with aqueous sodium dithionite or L-ascorbic acid in methanol. The reductive cleavage allowed to recover the [Co II(3)] complex in good yield, which could be easily re-oxidized to [CoIII(3)(OAc)] with air/AcOH and reused with essentially no loss of reactivity and selectivity. Investigation on the nitrogen substitution indicates that the presence of a single benzyl group on the amino acid nitrogen is important to obtain high enantioselectivity in the extraction process. The kinetic vs. thermodynamic nature of the resolution process was also investigated with an enantiomeric exchange experiment, which shows that the liquid-liquid extraction with [CoIII(3)-(OAc)] is an equilibrium process operating under thermodynamic control. In the absence of a suitable crystal structure of the [CoIII(3)(N-Bn-AA)] complexes, computational and spectroscopic studies were used to investigate how the N-benzyl α-amino acids are accommodated in the "binding pocket" of the chiral cobalt complex. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Primordial reductive amination revisited

Amino acids are formed efficiently by reductive amination of α-keto acids under aqueous, conditions with freshly precipitated FeS or Fe(OH)2 and with NH3, CH3NH2 or (CH3)2NH at pH values near their pKa.

Amino acid-derived cyclic phosphonamides and methods of synthesizing the same

New phosphonamide compounds and methods of forming those compounds are provided. In one embodiment, the inventive methods comprise subjecting an opened-ring phosphonamide template to a ring-closing metathesis reaction in the presence of a ring-closing catalyst (e.g., a Grubbs catalyst) to yield a phosphonamide. In another embodiment, the inventive methods comprise reacting a template structure with a phosphorus (III) compound to yield the phosphonamide. Advantageously, in either embodiment, the template structures can be provided with a wide array of functional groups (e.g., amino acid side chains, peptides) chosen to provide particular properties to the compound.

The Determination of Chirality of N-Methyl- and N,N-Dimethyl-phenylalanine by G.L.C.

The chirality of N-methylphenylalanine enantiomers can be determined on a micro scale by g.l.c. of N-pentafluoropropionyl amino acid isopropyl esters on a Chirasil-L-Val capillary column.N,N-Dimethylphenylalanine enantiomers cannot be similarly derivatize

Nummularine-O, a cyclopeptide alkaloid from Zizyphus nummularia

In addition to the known peptide alkaloid jubanine-B, a new peptide alkaloid, nummularine-O, has been isolated from the stem bark of Zizyphus nummularia and their structures have been elucidated by chemical and spectroscopic methods.