37661-60-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-N-Cbz-4-Methyl-5-oxooxazolidine is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of various drugs. Its chiral center allows for the creation of enantiomer-specific compounds, which can have different biological activities and are crucial in the design of effective medications.
Used in Organic Synthesis:
(S)-N-Cbz-4-Methyl-5-oxooxazolidine is used as a building block in organic synthesis for its versatility in creating complex molecular structures. This makes it an essential component in the development of new organic compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 50-00-0 formaldehyd 
• 1142-20-7 N-Cbz-Ala 
• 23632-66-8 (4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one 
• 26607-51-2 N-benzyloxycarbonyl-D-alanine 
• 501-53-1 benzyl chloroformate 
• 110-88-3 1,3,5-Trioxan 

Downstream Products

• 3913-67-5 N-methylalanine 
• 21691-41-8 (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid 
• 335660-20-3 (S)-5-Hydroxy-4-methyl-oxazolidine-3-carboxylic acid benzyl ester 
• 871917-79-2 benzyl {(1S)-2-[3,5-bis(trifluoromethyl)phenyl]-1-methyl-2-oxoethyl}carbamate 
• 1188391-99-2 (2S)-N-benzyloxycarbonyl-2-aminobut-2-methyl-3-enylpropanoic acid 
• 1188391-81-2 (2S)-N-benzyloxycarbonyl-2-aminobut-3-enylpropanoic acid 
• 5673-69-8 N-benzyloxycarbonyl-L-alanyl-L-alanine ethyl ester 
• 263908-29-8 (4S,5S)-4-Methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis method of silodosin

The invention discloses a synthesis method of silodosin. The synthesis method comprises the following steps of: sequentially performing amino protection, bromination and deprotection on indoline serving as a raw material; carrying out an SN2 reaction to o

Method for synthesizing metaraminol bitartrate

The invention provides a process for synthesizing metaraminol bitartrate. The process comprises the following steps: taking carbobenzoxy-L-alanine as a raw material, carrying out a cyclization reaction, and carrying out a reaction with a Grignard reagent so as to prepare an intermediate (4S)-N-carbobenzoxy-5-(3-(benzyloxy)phenyl)-5-hydroxy-4-methyloxazolane; carrying out a hydrolytic ring-opening reaction on the intermediate, and producing (2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-acetone; carrying out a reduction reaction on the (2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-acetone so as to obtain (1R,2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-propanol; performing deprotection on the (1R,2S)-2-(carbobenzoxy)amino-1-(3-benzyloxyphenyl)-1-propanol so as to obtain metaraminol; finally, performing salt formation on metaraminol and L-tartaric acid, thereby obtaining the metaraminol bitartrate. According to the method disclosed by the invention, usage of an expensive catalyst and chiral resolution can be avoided, and the cost is greatly reduced; by utilizing chemical synthesis, industrial production of optical pure metaraminol bitartrate becomes possible.

Method for preparing arene beta-amino alcohol of optical voidness

The invention discloses a method for preparing arene beta-amino alcohol of optical voidness. The method is characterized by comprising the following steps that a D or L-amino acid initial material reacts with benzyl chloroformate CBz-Cl or BOC acid anhydr

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.

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.

An enantioselective synthesis of (1S,2S)-pseudoephedrine

Synthesis of (1S,2S)-pseudoephedrine is described via reduction of an alanine-derived oxazolidinone followed by treating with phenyl magnesium bromide and chemoselective N-methylation in an efficient and practical manner. (C) 2000 Elsevier Science Ltd.

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

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.

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