853017-06-8

Upstream product

• 100-39-0 benzyl bromide 
• 3844-54-0 L-2-aminohexanoic acid-methyl ester hydrochloride 
• 206358-48-7 (2'RS,4S,5R)-1-N-(2'bromohexanoyl)-3,4-dimethyl-5-phenylimidazolidin-2-one 
• 445298-99-7 (S,S)-N-methylpseudoephedrine α-bromo-α-n-butylacetate 
• 100-46-9 benzylamine 
• 622-79-7 benzyl azide 
• 81801-15-2 (R)-(E)-3-octen-2-ol 
• 67-56-1 methanol 
• 206358-56-7 (4S,5R)-1-((R)-2-Benzylamino-hexanoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 

Downstream Products

• 923293-27-0 N-tert-butoxycarbonyl-L-phenylalanyl-N-benzyl-L-norleucine methyl ester 

Relevant academic research and scientific papers

Synthesis of functionalized, unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketopiperazines

A general and efficient method for the synthesis of unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketopiperazines (DKPs) is described. Cyclization of N-amide alkylated dipeptide methyl esters, followed by alkylation, furnished the corresponding tetrasubsti

Thermal and catalyzed [3,3]-phosphorimidate rearrangements

[3,3]-Sigmatropic rearrangements have been widely utilized for the synthesis of structurally complex organic molecules because of the ease with which carbon-carbon bonds are formed in a regio-and stereocontrolled manner. However, there are far fewer [3,3]-rearrangements available for the selective formation of carbon-nitrogen bonds despite the enormous potential of such reactions for the preparation of stereodefined allylic amines. We describe here the scope and mechanism of a [3,3]-rearrangement of allylic phosphorimidates that provides access to stereodefined allylic amines of diverse structure. The reactive intermediate in the reaction, an allylic phosphorimidate, is produced in situ through the combination of readily available starting materials (allylic alcohols, chlorophosphites, and organic azides), rendering the reaction an efficient three-component process. Analogous to other [3,3]-rearrangements, the stereochemistry in an allylic alcohol starting material is transferred with fidelity to the allylic amine product and, further, allylic amines are produced as single olefin isomers. In addition, a crossover experiment indicates that the rearrangement is an intramolecular process. Finally, activation of the allylic moiety either through incorporation of electron-deficient functional groups or through the use of a transition-metal catalyst significantly facilitates the reaction and consequently the preparation of a wider range of substitution patterns.

Dynamic resolution of α-bromo-α-alkyl esters using N-methyl pseudoephedrine as a chiral auxiliary: Asymmetric syntheses of α-amino acid derivatives

N-Methyl pseudoephedrine mediated dynamic resolution of α-bromo-α-alkyl esters in nucleophilic substitution reaction has been investigated. Best results are obtained when α-bromo-α-alkyl esters 1, 4 and 5 are allowed to equilibrate before the addition of nucleophile. This simple epimerization-substitution sequence provides a practical protocol for asymmetric syntheses of α-amino acid derivatives 2, 7 and 8 up to 98:2 enantiomeric ratio.