58438-04-3

Basic information

• Product Name: Boc-3-(2-Naphthyl)-L-alanine
• Synonyms: BOC-ALA(2-NAPH)-OH;BOC-ALA(2-NAPHTHYL)-OH;BOC-ALA-BETA-(2-NAPHTHYL)-OH;BOC-2-NAL-OH;BOC-2-L-NAPHTHYLALANINE;BOC-3-(2-NAPHTHYL)-ALANINE;BOC-3-(2-NAPHTHYL)-L-ALANINE;N-BOC-3-(2-NAPHTHYL)-L-ALANINE
• CAS NO: 58438-04-3
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.36
• Product Categories: Amino Acids;Alanine [Ala, A];Unusual Amino Acids;Boc-Amino acid series;a-amino
• Mol File: 58438-04-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 92-95 °C(lit.)
• Boiling Point: 454.92°C (rough estimate)
• Flash Point: 263.6 °C
• Appearance: Off-white/Solid
• Density: 1.2164 (rough estimate)
• Vapor Pressure: 2.58E-11mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• Storage Temp.: −20°C
• Solubility: soluble in Ethanol
• PKA: 3.88±0.30(Predicted)
• BRN: 4326467
• CAS DataBase Reference: Boc-3-(2-Naphthyl)-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-3-(2-Naphthyl)-L-alanine(58438-04-3)
• EPA Substance Registry System: Boc-3-(2-Naphthyl)-L-alanine(58438-04-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 58438-04-3(Hazardous Substances Data)

Usage

Description

Boc-3-(2-Naphthyl)-L-alanine is a chemical compound that features a Boc-protected L-alanine moiety with a 2-naphthyl group attached to the third carbon. This unique structure makes it a valuable building block in organic synthesis and a versatile reagent in various applications.

Uses

Used in Pharmaceutical Industry:
Boc-3-(2-Naphthyl)-L-alanine is used as a reagent for the synthesis of dipeptidyl nitriles, which are potent and reversible inhibitors of Cathepsin C. This makes it a valuable component in the development of drugs targeting proteolytic enzymes, potentially leading to treatments for various diseases and conditions.
Used in Organic Synthesis:
Boc-3-(2-Naphthyl)-L-alanine is used as a key intermediate in the synthesis of complex organic molecules, particularly those with biological activity. Its unique structure allows for the creation of novel compounds with potential applications in various fields, such as medicine, agrochemistry, and materials science.
Used in Research and Development:
Boc-3-(2-Naphthyl)-L-alanine is used as a research tool in the study of enzyme inhibition, protein structure, and other biological processes. Its ability to act as a potent and reversible inhibitor of Cathepsin C makes it a valuable probe for understanding the mechanisms of enzyme function and the development of new therapeutic agents.

InChI:InChI=1/C18H21NO4/c1-18(2,3)23-17(22)19-15(16(20)21)11-12-8-9-13-6-4-5-7-14(13)10-12/h4-10,15H,11H2,1-3H3,(H,19,22)(H,20,21)/t15-/m0/s1

Upstream product

• 939-26-4 2-bromomethylnaphthyl bromide 
• 143218-07-9 ethyl 2-acetylamino-2-cyano-3-(naphthalen-2-yl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 63024-44-2 2-Amino-3-naphthalen-2-yl-propionic acid; hydrochloride 
• 6960-34-5 L-3-(2-naphthyl)alanine 
• 74651-77-7 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 37447-33-9 acetylamino-[2]naphthylmethyl-malonic acid diethyl ester 
• 636572-72-0 C₂₃H₂₉NO₆ 
• 58438-04-3 N-tert-butoxycarbonyl-3-(2-naphthyl)-alanine 
• 1393112-55-4 (S)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate 
• 1393112-51-0 (RS)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate 
• 172214-89-0 2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 
• 136015-50-4 2-Acetylamino-2-naphthalen-2-ylmethyl-malonic acid monoethyl ester 
• 37439-99-9 (S)-N-acetyl-3-(2-naphthyl)alanine 

Downstream Products

• 636572-72-0 C₂₃H₂₉NO₆ 
• 190908-91-9 (1-(S)-methylcarbamoyl-2-naphthalen-2-yl-ethyl)-carbamic acid tert-butyl ester 
• 200864-78-4 [(S)-1-(3-Morpholin-4-yl-propylcarbamoyl)-2-naphthalen-2-yl-ethyl]-carbamic acid tert-butyl ester 
• 190908-93-1 (R)-N⁴-Benzyloxy-2-isobutyl-N¹-((S)-1-methylcarbamoyl-2-naphthalen-2-yl-ethyl)-succinamide 
• 136015-54-8 (S)-3-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-naphthalen-2-yl-propionylamino)-hexanoylamino]-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid 
• 1269472-84-5 C₁₆H₁₇NO 
• 1269472-86-7 C₂₄H₂₇N₃*ClH 
• 1269472-83-4 (R)-5-(naphthalen-2-ylmethyl)pyrrolidin-2-one 
• 1269472-88-9 (R)-2-mesityl-5-(naphthalen-2-ylmethyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium chloride 
• 1269472-81-2 C₂₄H₂₉NO₆ 
• 176896-73-4 methyl (S)-2-[(tert-butoxycarbonyl)amino]-3-(naphthalen-2-yl)propanoate 
• 702692-53-3 C₄₃H₅₉N₃O₇ 
• 1393112-51-0 (RS)-S-ethyl 2-(tert-butoxycarbonylamino)-3-(naphthalen-2-yl)propanethioate 

Relevant articles and documents

ARYLPYRROLIDINE DICARBOXYLIC ACID AMIDE DERIVATIVE

PROBLEM TO BE SOLVED: To provide a pyrrolidine derivative capable of catalyzing an asymmetric oxidation reaction of an alkene compound. SOLUTION: There is provided an arylpyrrolidine dicarboxylic acid amide derivative exemplified by cat.A in the following formula. There is provided an asymmetric oxidation catalyst having optical purity of 50%. There is provided a manufacturing method of an optically active epoxy compound including contacting the compound with an alkene derivative in addition to a co-oxidant. There is provided a manufacturing method of an optically active epoxy compound, in which the alkene derivative is a substituted alkene derivative having a functional group containing N or O at 3 position of a double bond. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution

A double catalyst system (protease + base) was applied to the dynamic kinetic resolution (DKR) of isomeric 1- and 2-α-naphthyl-glycines and -alanines exploiting the in situ racemization of their thioesters. Due to the different C-acidity of the two sets of compounds, different experimental conditions have been devised to perform the simultaneous resolution/racemization process. In all cases, the racemic N-Boc-thioesters were converted into the aminoacids with an l-configuration almost quantitatively and with complete enantioselectivity. 2012 Elsevier Ltd.

Substituted alkyldiamine derivatives

The present invention relates to novel substituted alkyldiamine derivatives and pharmaceutically acceptable salts thereof which are useful tachykinin antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions including asthma, cough, and bronchitis.