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

General Description

(S)-2-Tert-butoxycarbonylamino-3-naphthalen-2-yl-propionic acid methyl ester is a chemical compound with potential pharmaceutical applications. It is a derivative of the amino acid phenylalanine and contains a naphthalene ring. (S)-2-TERT-BUTOXYCARBONYLAMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID METHYL ESTER is commonly used as a building block in the synthesis of various pharmaceutical drugs, particularly as a precursor for chiral molecules. Its unique structural features make it a valuable intermediate in the production of medicines and other biologically active compounds. Additionally, it may also have potential applications in medicinal chemistry research and drug discovery due to its unique properties and structural characteristics.

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

Downstream Products

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

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.