66866-64-6

Upstream product

• 50-00-0 formaldehyd 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 110-88-3 1,3,5-Trioxan 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 24210-19-3 methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate 

Downstream Products

• 6216-65-5 N-benzyloxycarbonyl-L-valinol 
• 291778-49-9 N-[(1S,2S)-3,3,3-trifluoro-2-hydroxy-1-(isopropyl)propyl]-carbamic acid benzyl ester 
• 344799-94-6 (4S,5S)-4-Isopropyl-5-trifluoromethyl-5-(trimethylsilyl)oxy-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 1188391-85-6 (2S)-N-benzyloxycarbonyl-2-aminobut-3-enyl-(3-methyl)butanoic acid 
• 291778-48-8 benzyl (4S,5R)-5-hydroxy-4-(propan-2-yl)-5-(trifluoromethyl)-1,3-oxazolidine-3-carboxylate 
• 1463-21-4 N-trifluoroacetyl-(S)-valine methyl ester 
• 914939-75-6 (3S)-4-methyl-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid 
• 914939-80-3 phenylmethyl [(1S)-3-diazo-1-(1-methylethyl)-2-oxopropyl]methylcarbamate 
• 42417-65-2 Z-MeVal-OH 

Relevant academic research and scientific papers

Stereoselective synthesis of chiral β-amino trifluoromethyl alcohol: Development of a manufacturing process for a key intermediate in the production of a novel elastase inhibitor, AE-3763

We have successfully synthesized chiral β-amino trifluoromethyl alcohol (2S,3S)-7a, which is a key intermediate in the production of AE-3763, by stereoselective reduction of N-Cbz-protected 5-hydroxy-5-(trifluoromethyl)- 1,3-oxazolidine 4 prepared from L-valine in 3 steps followed by alkaline hydrolysis. This new method can be applied to the industrial-scale synthesis of AE-3763.

A novel synthesis of N-but-3-enyl-α- and β-amino acids

N-But-3-enyl-α- and β-amino acids can be prepared by cleaving 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones in the presence of allylsilanes and boron trifluoride etherate at room temperature in good to excellent yields. Georg Thieme Verlag Stuttgart.

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.

Synthesis of new β-amino acids via 5-oxazolidinones and the arndt-eistert procedure

N-Methyl β-amino acids are potentially useful amino acid derivatives for incorporation in lead peptide therapeutics. The syntheses of five such compounds are presented. Their synthesis via 6-oxazinanones was low yielding. Alternatively, reductive cleavage of a 5-oxazolidinone gave the N-methyl β-amino acid, which was then homologated via an Arndt-Eistert procedure in high yield to give the N-methyl α-amino acid. CSIRO 2005.

OPTICALLY ACTIVE AMINE DERIVATIVE AND METHOD OF SYNTHESIS

A readily available and inexpensive natural α -amino acid is converted into a compound represented by formula (1), which is then reacted with an organometallic reagent represented by formula (2) to give an optically active 5-hydroxyoxazolidine represented by formula (3), which is then treated with an acid to provide an optically active aminoketone represented by formula (4). The product is then converted into an optically active aminoalcohol represented by formula (5) or (6) by, for example reduction.The above process can provide an optically active aminoalcohol represented by formula (5) or (6) useful as a production intermediate for a medicine or pesticide from a readily available and inexpensive natural α-amino acid as a starting material stereoselectively and stably with a higher optical purity and a lower cost without racemization. This invention can also provide an optically active 5-hydroxyoxazolidine represented by formula (3) and an aminoketone represented by formula (4) as important intermediates for production of the above product as well as preparation processes therefor.

Mild regeneration of the carboxylic group of amino acid alkyl esters by aqueous methanolic sodium hydrogen carbonate via 5-oxazolidinones

A simple racemization-free procedure allows the regeneration of the carboxylic acid group of amino acid alkyl esters by way of an intermediate 5-oxazolidinone which is hydrolyzed by treatment with sodium hydrogen carbonate in aqueous methanol.

Processes for producing (aminomethyl)trifluorocarbinol derivatives

The present invention provides a process for industrially producing (aminomethyl)trifluoromethylcarbinol derivatives, in particularly, optically active compounds thereof, which are useful as starting compounds for drugs such as protease inhibitors, etc.

HETEROCYCLIC COMPOUNDS, INTERMEDIATES THEREOF AND ELASTASE INHIBITORS

The present invention relates to a heterocyclic compound of the following formula (I-a), its ester, or a salt thereof, and a human neutrophilic elastase inhibitor containing the same as the active ingredient, etc. wherein A and B are the same or different

A novel, one-pot preparation of N-methyl-α-amino acid dipeptides from oxazolidinones and amino acids

A new synthetic method has been developed to prepare N-methyl dipeptides in one-pot directly from oxazolidinones. Treatment of oxazolidinone 1 with an amino ester yields an intermediate N-hydroxymethyl dipeptide 3, which is treated with TFAA and triethyls

Selective reductions of oxazolidinones: New protocol for diastereoselective synthesis of vicinal amino alcohols

Selective reductions of oxazolidinones using sodium borohydride and their application to the diastereoselective synthesis of vicinal amino alcohols are described.