176896-73-4

Basic information

• Product Name: (S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER
• Synonyms: (S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER;Methyl N-Boc-3-(naphthalen-2-yl)-L-alaninate
• CAS NO: 176896-73-4
• Molecular Formula: C₁₉H₂₃NO₄
• Molecular Weight: 329.39
• Mol File: 176896-73-4.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER(176896-73-4)
• EPA Substance Registry System: (S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER(176896-73-4)

Safety Data

• Hazardous Substances Data: 176896-73-4(Hazardous Substances Data)

Usage

Description

(S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER is a chemical compound derived from the amino acid phenylalanine, featuring a naphthalene ring. It is recognized for its potential pharmaceutical applications and unique structural features, making it a valuable intermediate in the synthesis of various pharmaceutical drugs and biologically active compounds.

Uses

Used in Pharmaceutical Industry:
(S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER is used as a building block for the synthesis of various pharmaceutical drugs, particularly as a precursor for chiral molecules. Its unique structural features contribute to the development of new medicines and enhance the production of biologically active compounds.
Used in Medicinal Chemistry Research:
(S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER is utilized in medicinal chemistry research and drug discovery due to its distinctive properties and structural characteristics. It aids in the exploration of novel drug candidates and the advancement of pharmaceutical drug development.

Upstream product

• 176794-85-7 (Z)-methyl 2-((tert-butoxycarbonyl)amino)-3-(naphthalen-2-yl)acrylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 109063-69-6 (S)-methyl 2-amino-3-(naphthalen-2-yl)propanoate 
• 56583-58-5 N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine 
• 74-88-4 methyl iodide 
• 6960-34-5 L-3-(2-naphthyl)alanine 
• 67-56-1 methanol 
• 58438-04-3 N-tert-butoxycarbonyl-3-(2-naphthyl)-alanine 
• 580-13-2 2-bromonaphthalene 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 42096-34-4 naphthalen-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 

Downstream Products

• 894407-00-2 (3S,4S)-3-[(tert-butyl)dimethylsiloxy]-5-(2-naphthyl)-4-[N-(2-nitrobenzenesulfonyl)amino]pent-1-ene 
• 894407-04-6 (5S,6S)-1-[4-(tert-butoxycarbonylamino)butyl]-5,6-dihydro-5-diphenylphosphoryloxy-6-[(2-naphthyl)methyl]pyridin-2-one 
• 894407-01-3 (3S,4S)-4-{N-[4-(tert-butoxycarbonylamino)butyl]-N-(2-nitrobenzenesulfonyl)}amino-3-[(tert-butyl)dimethylsiloxy]-5-(2-naphthyl)pent-1-ene 
• 842166-66-9 tert-butyl (2S)-[N-[2-[(tert-butoxy)carbonylamino]-3-(2-naphthyl)propyl](phenylmethoxy)carbonylamino]acetate 
• 842166-67-0 (2S)-[N-[2-[(fluoren-9-ylmethoxy)carbonylamino]-3-(2-naphthyl)propyl](phenylmethoxy)carbonylamino]acetic acid 
• 63024-26-0 methyl (S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride 

Relevant articles and documents

Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides

(Chemical Equation Presented) A combination of Pd2(dba) 3 and SPhos (1:2 molar ratio) is an excellent precatalyst for the Negishi cross-coupling of the serine-derived organozinc reagent 2 with aryl halides, including previously difficult ortho-substituted examples. In the case of meta- and para-substituted aryl halides, Pd-loadings of 0.5 mol % give satisfactory results. Use of 2-iodoaniline as substrate gives the lactam 12 in good yield. 2009 American Chemical Society.

Negishi cross-coupling reactions of α-amino acid-derived organozinc reagents and aromatic bromides

The Negishi cross-coupling reaction of organozinc iodides derived from α-amino acids with aromatic bromides to give substituted phenylalanine derivatives is described, using either Pd(OAc)2 or Pd2(dba)3 in combination with P(o-Tol)3 as catalyst in DMF at 50 °C. Similar results are obtained using Pd[PtBu3]2 as catalyst. The difference in reactivity displayed between aryl iodides and bromides (ArI>ArBr) has been utilised in a short synthesis of an unsymmetrical, orthogonally protected para-phenylene bis-alanine derivative.