55740-07-3

Upstream product

• 50-00-0 formaldehyd 
• 1161-13-3 N-Cbz-L-Phe 
• 110-88-3 1,3,5-Trioxan 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 

Downstream Products

• 117161-88-3 (4S,R)-3-(benzyloxycarbonyl)-4-(phenylmethyl)-4-<1-(2-propenyl)>-5-oxooxazolidine 
• 2899-07-2 (S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine 
• 191981-04-1 (4S,5S)-4-benzyl-N-(benzyloxycarbonyl)-5-(trifluoromethyl)-5-[(trimethylsilyl)oxy]-1,3-oxazolidine 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 220931-41-9 (S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester 
• 6372-14-1 N-((benzyloxy)carbonyl)-L-phenylalaninol 
• 224434-13-3 (S)-4-Benzyl-5-hydroxy-oxazolidine-3-carboxylic acid benzyl ester 
• 73048-81-4 benzyl (S)-(1-(hydroxyamino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 5241-56-5 benzyl [(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]carbamate 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 
• 28709-70-8 N-benzyloxycarbonyl-L-phenylalanine ethyl ester 
• 64286-85-7 N-(benzyloxycarbonyl)-L-phenylalanine allyl ester 
• 63-91-2 L-phenylalanine 
• 922705-73-5 phenylmethyl [(1S)-3-diazo-2-oxo-1-(phenylmethyl)propyl]methylcarbamate 

Relevant academic research and scientific papers

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.

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.

Microwave accelerated efficient synthesis of N-fluorenylmethoxycarbonyl/t-butoxycarbonyl/benzyloxycarbonyl-5- oxazolidinones

The synthesis of N-protected 5-oxazolidinones using amino acids, paraformaldehyde and p-toluene sulfonic acid in a minimum amount of toluene accelerated by microwave irradiation for 3 min in high yield is described.

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.

A simple and rapid protocol for N-methyl-α-amino acids

A two step strategy for optically pure N-Protected-N-methyl-α-amino acids starting from N-protected-α-amino acids via reductive cleavage of oxazolidinones using NaCNBH3/TMSCl is described.

A Novel, Facile and Diastereoselective Synthesis of (3S,4S) and (3R,4S)-N-Me-AHPPA

Diastereoselective syntheses of (3S,4S) and (3R,4S)-N-methyl-AHPPA are achieved via a novel Wittig reaction of an oxazolidinone followed by reduction.

Reaction of (Trifluoromethyl)trimethylsilane with Oxazolidin-5-ones: Synthesis of Peptidic and Nonpeptidic Trifluoromethyl Ketones

(Trifluoromethyl)trimethylsilane (TMS-CF3, the Ruppert Reagent) reacts with a variety of amino acid derived N-substituted oxazolidin-5-ones in excellent yields. Mild acid hydrolysis of adducts with electron-releasing substituents at C-2 affords

A practical approach for the optically pure N-Methyl-α- amino acids

A new practical synthesis of N-Methyl-α-amino acids by racemization free methodology has been developed. The method involves the reductive cleavage of N-protected oxazotidinones using hydrogen in the presence of Pd/C to give the title compounds in quantitative yields.