111771-58-5

Basic information

• Product Name: BOC-ALPHA-METHYL-L-PHE
• Synonyms: BOC-(S)-2-AMINO-2-METHYL-3-PHENYLPROPANOIC ACID;BOC-ALPHA-METHYL-L-PHE;BOC-ALPHA-METHYL-L-PHENYLALANINE;BOC-ALPHA-BENZYL-L-ALA;N-BOC-ALPHA-METHYL-L-PHENYLALANINE;N-BOC-A-METHYL-L-PHENYLALANINE;Boc-alphaMe-L-Phe-OH;Boc-α-methyl-L-phenylalanine
• CAS NO: 111771-58-5
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Unusual amino acids;unnatural amino acids
• Mol File: 111771-58-5.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 432.1±38.0 °C(Predicted)
• Appearance: /
• Density: 1.140±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.92±0.11(Predicted)
• CAS DataBase Reference: BOC-ALPHA-METHYL-L-PHE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ALPHA-METHYL-L-PHE(111771-58-5)
• EPA Substance Registry System: BOC-ALPHA-METHYL-L-PHE(111771-58-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 111771-58-5(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Boc-α-methyl-L-phenylalanine was a useful reagent in discovery of oxadiazoyl tertiary carbinamine inhibitors of β-?secretase (BACE-?1)?. It was also used in the study for strategies toward improving the brain penetration of macrocyclic tertiary carbinamine BACE-1 inhibitors.

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 178457-42-6 benzyl (R)-2-amino-2-methyl-3-phenylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 361521-82-6 benzyl (R)-2-(tert-butoxycarbonylamino)-2-methyl-3-phenylpropanoate 
• 17350-84-4 (R)-2-amino-2-methyl-3-phenylpropanoic acid 
• 1443008-10-3 (S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethyl-3-phenylpropanamide 
• 1132-26-9 2-methyl-3-phenylalanine 
• 64384-47-0 2-amino-3-phenyl-2-methylpropanenitrile 
• 103-79-7 1-phenyl-acetone 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 1393737-29-5 (S)-4-benzyl-3-tert-butoxycarbonyl-4-methyl-2-oxazolidinone 
• 1393737-59-1 (S)-4-benzyl-4-methyl-2-oxazolidinone 

Downstream Products

• 192064-93-0 (S)-2-((S)-2-tert-Butoxycarbonylamino-2-methyl-3-phenyl-propionylamino)-3-(1H-imidazol-4-yl)-propionic acid methyl ester 
• 361521-83-7 [(R)-2-(tert-butoxycarbonylamino)-2-methyl-3-phenylpropanoyl]-L-alanine benzyl ester 
• 868286-30-0 R-N-(tert-butoxycarbonyl)-α-methylphenylalaninamide 
• 925455-53-4 tert-butyl (1R)-1-benzyl-2-{2-[(7-ethyl-1-methyl-2,2-dioxido-3,4-dihydro-1H-[1,2,5]thiadiazepino[3,4,5-hi]indol-9-yl)carbonyl]hydrazino}-1-methyl-2-oxoethylcarbamate 
• 1428736-37-1 (2S)-2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropanamide 
• 1428736-40-6 (2R,5S)-5-benzyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-42-8 (2S,5S)-5-benzyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-44-0 (2R,5S)-5-benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-46-2 (2S,5S)-5-Benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 868286-97-9 C₃₂H₄₄N₄O₆S 
• 868286-98-0 C₃₂H₄₂N₄O₅S 
• 868287-01-8 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)-N-((R)-1-(4-fluorophenyl)ethyl)benzamide 
• 868286-95-7 C₃₃H₃₉FN₆O₅S 
• 868286-93-5 C₃₃H₃₈FN₅O₆S 

Relevant articles and documents

Diastereoselective Alkylation of Sultam-Derived Amino Acid Aldimines Preparation of Cα-Methylated Amino Acids

Alkylation of Schiff bases 2 derived from 4-chlorobenzaldehyde and sultam-derived amino acids 1 gave crystalline diastereomers 3 which after deprotection and re-crystallization, if necessary, afforded in good yield enantiomerically pure Cα-methylated amin

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl) imidazolidine-4-one ligands

Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (α-methylDOPA and α- methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectivity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention.