37661-60-2

Basic information

• Product Name: (S)-N-Cbz-4-Methyl-5-oxooxazolidine
• Synonyms: (S)-N-Cbz-4-Methyl-5-oxooxazolidine;Benzyl (4S)-4-methyl-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS NO: 37661-60-2
• Molecular Formula: C₁₂H₁₃NO₄
• Molecular Weight: 235.23592
• Mol File: 37661-60-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-N-Cbz-4-Methyl-5-oxooxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Cbz-4-Methyl-5-oxooxazolidine(37661-60-2)
• EPA Substance Registry System: (S)-N-Cbz-4-Methyl-5-oxooxazolidine(37661-60-2)

Safety Data

• Hazardous Substances Data: 37661-60-2(Hazardous Substances Data)

Usage

General Description

(S)-N-Cbz-4-Methyl-5-oxooxazolidine, also known as (S)-4-Methyl-5-oxooxazolidine-2-carboxylic acid benzyl ester, is a chemical compound with the molecular formula C13H15NO4. It is a white to off-white solid and is typically used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. (S)-N-Cbz-4-Methyl-5-oxooxazolidine has a chiral center and exists as a pair of enantiomers, with the (S)-enantiomer having specific applications in organic synthesis. (S)-N-Cbz-4-Methyl-5-oxooxazolidine is often used as a building block in the synthesis of various drugs and is important in the field of medicinal chemistry.

Upstream product

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

Downstream Products

• 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 
• 159016-47-4 ((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamic acid benzyl ester 
• 104863-92-5 (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol 
• 335660-26-9 (S)-5-Acetoxy-4-methyl-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

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 preparing arene beta-amino alcohol of optical voidness

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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.