63096-02-6

Basic information

• Product Name: BOC-LEU-OME
• Synonyms: 3-[(2-acetamido-3-phenyl-propanoyl)amino]benzoic acid;Boc-L-Leucine methyl;L-Leucine, N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester;N-Boc-L-leucine Methyl ester, 97%;Methyl N-(tert-butoxycarbonyl)-L-leucinate;(2S)-2-(tert-Butoxycarbonylamino)-4-methylpentanoic acid methyl ester;N-(tert-Butyloxycarbonyl)leucine methyl ester;(S)-Methyl 2-((tert-butoxycarbonyl)aMino)-4-Methylpentanoate
• CAS NO: 63096-02-6
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.32
• Product Categories: Amino Acid Derivatives;Leucine;Peptide Synthesis
• Mol File: 63096-02-6.mol

Chemical Properties

• Melting Point: 147-149℃
• Boiling Point: 205 °C(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 0.991 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000278mmHg at 25°C
• Refractive Index: n20/D 1.44(lit.)
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: BOC-LEU-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-LEU-OME(63096-02-6)
• EPA Substance Registry System: BOC-LEU-OME(63096-02-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 63096-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-LEU-OME is used as a synthetic intermediate for the preparation of heterocyclic compounds, specifically as hematopoietic prostaglandin D synthase (H-PGDS) inhibitors. These inhibitors play a crucial role in the development of drugs targeting inflammatory and allergic diseases by modulating the synthesis of prostaglandin D2, a key mediator in these conditions.

InChI:InChI=1/C12H23NO4/c1-8(2)7-9(10(14)16-6)13-11(15)17-12(3,4)5/h8-9H,7H2,1-6H3,(H,13,15)/t9-/m0/s1

Upstream product

• 100-36-7 N,N-diethylethylenediamine 
• 395647-21-9 N-{3-[(N,N-dimethylaminophenyl)-4'-diazenyl]benzoyl}-N-tert-butyloxycarbonylleucine methyl ester 
• 69805-63-6 methyl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate 

Downstream Products

• 58521-45-2 tert-butoxycarbonyl-L-leucinal 
• 33900-15-1 (2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-[(tert-butoxycarbonyl)amino]-4-methylpentanamide 
• 51021-87-5 N-benzyloxycarbonyl-L-leucine methyl ester 
• 62023-30-7 DL-threo-3-amino-2-hydroxy-5-methylhexanoic acid 
• 2666-93-5 (S)-Leu-OMe 
• 82010-31-9 (S)-(1-hydroxymethyl-3-methylbutyl)carbamic acid tert-butyl ester 
• 1027137-63-8 [(2R,4S,5S)-5-(N-Boc-L-phenylalanylamido)-4-hydroxy-2,7-dimethyloctanoyl] N'-isobutyl amide 
• 637024-68-1 N-(2-azido-5-hydroxy-1-isobutyl-4-methyl-pentyl)-N',N'-dipropyl-isophthalamide 
• 637024-85-2 (2R,4S,5S)-4-Azido-5-(3-dipropylcarbamoyl-benzoylamino)-2,7-dimethyl-octanoic acid 
• 1026705-78-1 N-[2-azido-4-(1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-isobutyl-pentyl]-N',N'-dipropyl-isophthalamide 

Relevant articles and documents

Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids

Protease catalysed hydrolysis of N-Boc-amino acid esters allows us to obtain N-Boc l-acids and d-esters of amino butanoic acid, nor-leucine, nor-valine, leucine and t-leucine in excellent ee. The reaction occurs in short reaction times and high concentrations. When a biphasic system (buffer-MTBE) is employed, a strong solvent effect is observed. This method could be of significance for the preparation of d-t-leucine, for which a practical method is currently unavailable.

Development of a temporary marker for peptides

3-[(N,N-Dimethylaminophenyl)-4′-diazenyl]benzoic acid was coupled with several amino acid esters and the product acylated further with Boc. The material thus obtained was then submitted to cleavage by electrolysis and nucleophilic attack in order to evaluate the possibility of using this chromophore as a temporary marker.

A temporary marker for biological applications

Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.