97534-82-2

Usage

Chemical Properties

White powder

InChI:InChI=1/C12H13NO5/c14-11(15)10-7-17-8-13(10)12(16)18-6-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,15)/t10-/m0/s1

Upstream product

• 45521-08-2 (S)-oxazolidine-4-carboxylic acid 
• 501-53-1 benzyl chloroformate 
• 50-00-0 formaldehyd 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 

Downstream Products

• 126111-22-6 (S)-3-<(phenylmethoxy)carbonyl>-4-oxazolidinecarboxylic acid methyl ester 
• 258830-27-2 (S)-4-(N-Methoxy-N-methylcarbamoyl)oxazolidine-3-carboxylic acid benzyl ester 
• 258830-35-2 (S)-4-[(E)-3-(N,N-Diethylamino)propenoyl]oxazolidine-3-carboxylic acid benzyl ester 
• 258830-31-8 (S)-4-[3-(Trimethylsilanyl)propynoyl]oxazolidine-3-carboxylic acid benzyl ester 
• 299430-79-8 (S)-4-(1-Phenyl-1H-pyrazol-3-yl)oxazolidine-3-carboxylic acid benzyl ester 
• 299430-82-3 (S)-4-(1-Phenyl-1H-pyrazol-5-yl)oxazolidine-3-carboxylic acid benzyl ester 
• 299430-80-1 (S)-[2-Hydroxy-1-(1-phenyl-1H-pyrazol-3-yl)ethyl]carbamic acid benzyl ester 
• 299430-83-4 (S)-[2-Hydroxy-1-(1-phenyl-1H-pyrazol-5-yl)ethyl]carbamic acid benzyl ester 
• 1307877-46-8 (-)-(S)-benzyl 4-[(2,6-dimethylphenyl)carbamoyl]-1,3-oxazolidine-3-carboxylate 
• 258830-56-7 (R)-4-[1-((S)-1-Carboxy-2-phenyl-ethyl)-1H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258833-67-9 (S)-2-[5-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-phenyl-propionic acid methyl ester 
• 258833-79-3 (S)-2-[3-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-phenyl-propionic acid methyl ester 
• 258830-44-3 (R)-4-[2-((S)-1-Carboxy-2-phenyl-ethyl)-2H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of N-protected N-methyl serine and threonine

Two efficient and convenient syntheses of N-Cbz and N-Fmoc N-methyl serine and threonine are described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone.

The facile production of N-methyl amino acids via oxazolidinones

A range of oxazolidinones derived from N-carbamoyl α-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most α-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl α-amino acids. CSIRO 2000.

Optically Active 4-Oxaproline Derivatives: New Useful Chiral Synthons Derived from Serine and Threonine

A very simple procedure for the preparation of chiral optically active N-protected-4-carboxy-1,3-oxazolidine (4-oxaproline) derivatives starting from serine and threonine is described which avoids the use of toxic solvents or reagents.Elaboration of these compounds allows significant improvement in the handling of serine and threonine during the multigram preparation of oligopeptide structures and affords versatile chiral building blocks for the organic synthesis.

(Phosphinyloxy)acid amino acid inhibitors of angiotensin converting enzyme. 2. Terminal amino acid analogues of (S)-1-[6-Amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]- L-proline

Analogues of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]- L-proline (1, SQ 29,852) in which the terminal proline residue has been replaced by a variety of substituted and heteroatom-substituted prolines, N-arylglycines, N-cycloalkylglycines, and bicyclic amino acids have been synthesized and evaluated as inhibitors of angiotensin converting enzyme in vitro an in vivo. In general, the addition of lipophilic substituents to the 4-position of proline of the parent phosphate 1 resulted in substantial increases in vitro activity. The largest improvements were observed in the case of cis-benzyl (36-fold) and dithioketal (24-fold) analogues 2r and 2x, respectively. These enhancements of in vitro activity were accompanied by modest increases (2-3.5-fold) in in vivo (iv) activity. Among the various terminal amino acid replacements examined in this study, the indoline-based analogue 2i was by far the most potent compound on iv administration in the normotensive rat.