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

Description

BOC-ALPHA-METHYL-L-PHE, also known as Boc-α-methyl-L-phenylalanine, is a synthetic amino acid derivative characterized by a white powder appearance. It features a protecting group (BOC) and a methyl group substitution on the alpha carbon of the L-phenylalanine molecule, which contributes to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Research:
BOC-ALPHA-METHYL-L-PHE is used as a reagent in the discovery of oxadiazoyl tertiary carbinamine inhibitors of β-secretase (BACE-1). It plays a crucial role in the development of potential therapeutic agents targeting Alzheimer's disease by inhibiting the enzyme responsible for amyloid-beta peptide production.
Used in Medicinal Chemistry:
BOC-ALPHA-METHYL-L-PHE is utilized in the study of strategies aimed at improving the brain penetration of macrocyclic tertiary carbinamine BACE-1 inhibitors. This research is vital for enhancing the effectiveness of drugs designed to cross the blood-brain barrier and treat neurological disorders, such as Alzheimer's disease.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 1393737-24-0 diethyl 2-benzyl-2-(N-((S)-α-methylbenzyl)amino)malonate 
• 1393737-36-4 (S)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol 
• 1393737-40-0 (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone 
• 1393737-47-7 (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone 
• 1393737-23-9 diethyl 2-benzyl-2-(N-((S)-α-methylbenzyl)amino)malonate hydrochloride 
• 1393737-50-2 (S)-(4-benzyl-2-oxazolidinon-4-yl)methyl p-toluenesulfonate 
• 1393737-59-1 (S)-4-benzyl-4-methyl-2-oxazolidinone 
• 1393737-29-5 (S)-4-benzyl-3-tert-butoxycarbonyl-4-methyl-2-oxazolidinone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 103-79-7 1-phenyl-acetone 
• 64384-47-0 2-amino-3-phenyl-2-methylpropanenitrile 

Downstream Products

• 74814-07-6 Tyr-D-Ala-Gly-Phe(αMe) 
• 74814-06-5 Tyr-D-Ala-Gly-Phe(αMe)-Leu 
• 118111-40-3 (2R)-(+)-N-<(1,1-dimethylethyl)oxycarbonyl>-2-methyl-3-phenylalanine N-hydroxysuccinimide ester 
• 129713-59-3 N-tert-butoxycarbonyl-L-α-methylphenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester 
• 74825-82-4 tert-butoxycarbonyl-α-methyl-L-phenylalanyl-L-valine benzyl ester 
• 129713-59-3 N-tert-butoxycarbonyl-D-α-methylphenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester 
• 111771-59-6 Boc-D-α-methylphenylalanine dicyclohexylamine salt 
• 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 
• 804547-92-0 N-(tert-butoxycarbonyl)-D-α-methylphenylalanyl-L-proline benzyl ester 
• 928330-65-8 2-tert-butoxycarbonylamino-2-methyl-3-phenyl-propionic acid 3-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-5-(methanesulfonyl-methyl-amino)-benzyl ester 
• 868286-83-3 (1-{5-[3-[1-(4-fluoro-phenyl)-ethylcarbamoyl]-5-(methanesulfonyl-methyl-amino)-phenyl]-[1,3,4]oxadiazol-2-yl}-1-methyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 179747-18-3 N-(tert-butoxycarbonyl)-D-α-methylphenylalanyl-L-proline 
• 118203-65-9 C₁₄H₁₆⁽²⁾H₂N₂O₃*CH₂O₂ 

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.

Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine

The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.