138867-51-3

Basic information

• Product Name: D-Phenylalanine, N-(phenylacetyl)-, methyl ester
• CAS NO: 138867-51-3
• Molecular Formula: C18H19NO3
• Molecular Weight: 297.354
• Mol File: 138867-51-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: D-Phenylalanine, N-(phenylacetyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Phenylalanine, N-(phenylacetyl)-, methyl ester(138867-51-3)
• EPA Substance Registry System: D-Phenylalanine, N-(phenylacetyl)-, methyl ester(138867-51-3)

Safety Data

• Hazardous Substances Data: 138867-51-3(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63060-94-6 D-phenylalanine ethyl ester hydrochloride 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 103-80-0 phenylacetyl chloride 
• 21685-51-8 D-phenylalanine methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 1130067-28-5 C₁₈H₁₇NO₂ 
• 21685-51-8 D-phenylalanine methyl ester 

Relevant articles and documents

A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids

The development of direct and atom-economical amidation methods is of high priority because of the importance of amides and peptides as components of pharmaceuticals and commodity chemicals. This article describes the identification of more economical and more practical conditions for direct amidation of carboxylic acids and amines using the MIBA catalyst (5-methoxy-2-iodophenylboronic acid, 6) and its application to the coupling of α- and β-amino acid derivatives. It is now possible to use half of the quantity of molecular sieves prescribed in the original procedure, at a higher concentration leading to a reduction of waste and a substantially improved E-factor. This procedure was validated in the multigram scale preparation of prototypical amides, including aminoacids, using toluene as the solvent. Because of substrate inhibition of the catalyst with monoprotected α-aminoacids, the use of doubly-protected N-phthaloyl α-aminoacids or α-azidoacids is required in order to produce dipeptide products in moderate yields. β-Aminoacids do not suffer from this problem, and Boc-β-aminoacids can be coupled successfully. Unlike other boronic acid catalysts, 6 is active under ambient and low-heat conditions, which helps prevent any epimerization of chiral α-aminoacid derivatives.

Borate esters as convenient reagents for direct amidation of carboxylic acids and transamidation of primary amides

Simple borates serve as effective promoters for amide bond formation with a variety of carboxylic acids and amines. With trimethyl or tris(2,2,2- trifluoroethyl) borate, amides are obtained in good to excellent yield and high purity after a simple work-up procedure. Tris(2,2,2-trifluoroethyl) borate can also be used for the straightforward conversion of primary amides to secondary amides via transamidation. The Royal Society of Chemistry 2011.

Quantitative enzymatic protection of D-amino acid methyl esters by exploiting 'relaxed' enantioselectivity of penicillin-G amidase in organic solvent

A quantitative method for enzymatic protection of esters of various d-amino acids in organic solvent is reported. The lower enantioselectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various d-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site.