1201683-62-6

Basic information

• Product Name: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoate
• Synonyms: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoate
• CAS NO: 1201683-62-6
• Molecular Weight: 313.781
• Mol File: 1201683-62-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoate(1201683-62-6)
• EPA Substance Registry System: methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chlorophenyl)propanoate(1201683-62-6)

Safety Data

• Hazardous Substances Data: 1201683-62-6(Hazardous Substances Data)

Upstream product

• 615-41-8 2-iodochlorobenzene 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 114873-02-8 N^α-[(tert-butoxy)carbonyl]-2-(chloro)-L-phenylalanine 
• 74-88-4 methyl iodide 

Downstream Products

• 1240613-18-6 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 
• 1240613-19-7 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 

Relevant articles and documents

Evidence for the role of tetramethylethylenediamine in aqueous negishi cross-coupling: Synthesis of nonproteinogenic phenylalanine derivatives on water

The structure of the alkylzinc-tetramethylethylenediamine (TMEDA) cluster cation 3 has been determined in the gas phase by a combination of tandem mass spectrometry, infrared multiphoton dissociation (IRMPD) spectroscopy, and DFT calculations. Both sets of experimental results establish the existence of a strongly stabilizing interaction of TMEDA with the zinc cation. High-level DFT calculations on the alkylzinc-TMEDA cluster cation 3 allowed the identification of two low energy conformers, each featuring a four-coordinate zinc atom with a bidentate TMEDA ligand, and internal coordination from the carbonyl group of the Boc group to zinc. The experimental IRMPD spectrum is reproduced with an appropriately weighted combination of the IR spectra of the two conformers identified by theory. DFT calculations on the structure of the alkylzinc halide 2 with coordinated TMEDA using the PCM model of water solvent suggest that TMEDA can promote ionization of the zinc-iodine bond in organozinc iodides under aqueous conditions, providing a credible explanation for the role of TMEDA in stabilizing the carbon-zinc bond. Reaction of the serine-derived iodide 1 with aryl iodides "on water", promoted by nano zinc in the presence of PdCl2 (Amphos) 2 (5 mol %) and TMEDA, leads to the formation of protected phenylalanine derivatives 4 in reasonable yields. In the case of ortho-substituted aryl iodides and aryl iodides that are solids at room temperature, conducting the reaction at 65°C gives improved results. In all cases, the product 5 of reductive dimerization of the iodide 1 is also isolated.

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.