949-45-1

Basic information

• Product Name: (S)-3-phenyl-2-ureido-propionic acid
• Synonyms: (S)-3-phenyl-2-ureido-propionic acid
• CAS NO: 949-45-1
• Molecular Weight: 208.217
• Mol File: 949-45-1.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (S)-3-phenyl-2-ureido-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-phenyl-2-ureido-propionic acid(949-45-1)
• EPA Substance Registry System: (S)-3-phenyl-2-ureido-propionic acid(949-45-1)

Safety Data

• Hazardous Substances Data: 949-45-1(Hazardous Substances Data)

Upstream product

• 37534-65-9 D-2-carbamoylamino-3-phenylpropionic acid 
• 3530-82-3 5-benzyl-hydantoin 
• 673-06-3 D-(R)-phenylalanine 
• 1738-78-9 L-phenylalanine benzyl ester p-toluene-sulfonic acid salt 
• 63-91-2 L-phenylalanine 
• 57-13-6 urea 
• 40857-14-5 (5S)-(phenylmethyl)-2,4-imidazolidinedione 
• 17585-69-2 L-phenylalanine hydrochloride 
• 590-28-3 potassium cyanate 

Downstream Products

• 14825-82-2 L-phenylalanine-N-carboxyanhydride 
• 1118428-87-7 C₂₈H₂₈N₄O₄ 
• 1118428-86-6 C₂₈H₂₈N₄O₄ 
• 40857-14-5 (5S)-(phenylmethyl)-2,4-imidazolidinedione 
• 1020666-19-6 tert-butyl 7-((S)-1-carboxy-2-phenylethyl)-6,8,10-trioxo-1,7,9-triaza-spiro[4.5]decane-1-carboxylate 
• 196513-42-5 Methyl (2S)-N-(benzyloxycarbonylamino)-N-((2S)-N-chloroacetylprolyl)phenylalaninate 
• 175853-44-8 (9aS)-2-((1S)-1-Methoxycarbonyl-2-phenylethyl)-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo[2,1-d][1,2,5]triazepine-1,5-dione 
• 143689-85-4 Methyl (2S)-N-(benzyloxycarbonylamino)phenylalaninate 
• 154006-07-2 (S)-2-(2-((benzyloxy)carbonyl)hydrazinyl)-3-phenylpropanoic acid 
• 258830-56-7 (R)-4-[1-((S)-1-Carboxy-2-phenyl-ethyl)-1H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258833-67-9 (S)-2-[5-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-phenyl-propionic acid methyl ester 
• 258833-79-3 (S)-2-[3-((R)-1-Benzyloxycarbonylamino-2-hydroxy-ethyl)-pyrazol-1-yl]-3-phenyl-propionic acid methyl ester 
• 258830-44-3 (R)-4-[2-((S)-1-Carboxy-2-phenyl-ethyl)-2H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid benzyl ester 
• 258830-50-1 4-[1-(1-carboxy-2-phenyl-ethyl)-1H-pyrazol-3-yl]-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant articles and documents

Efficient syntheses of 13C- and 14C-labelled 5-benzyl and 5-indolylmethyl L-hydantoins

Robust and straightforward methods are described for the first syntheses of highly pure 13C- and 14C-labelled L-5-benzylhydantoin (L-BH) and L-5-indolylmethylhydantoin (L-IMH) by cyclizing the amino acids L-phenylalanine and L-trypto

Rapid and efficient microwave-assisted synthesis of N-carbamoyl-L-amino acids

A rapid and efficient method for the synthesis of N-carbamoyl-L-amino acids is reported. The procedure, involving the reaction between urea and α-amino acids sodium salts, was performed under microwave conditions using an unmodified domestic microwave oven. A careful study of the operative conditions indicated proline (1d) as the less reactive substrate and phenylglycine (1e) as the more reactive one among all the α-amino acids tested. Substitution of urea with potassium cyanate produced a low conversion into the corresponding N-carbamoyl derivative, and a possible explanation of this result is reported. Copyright Taylor & Francis Group, LLC.

A pH-dependent cyanate reactivity model: Application to preparative N-carbamoylation of amino acids

Recent developments in peptide synthesis have underlined the importance of optimising, on a preparative scale, the N-carbamoylation of amino acids by aqueous cyanate. To this purpose, a theoretical model of aqueous cyanate reactivity was designed. The parameters of the model were evaluated, for various pH and temperatures, from a critical survey of the literature, together with additional experimental data. Computer-simulated kinetics based on this model showed the reaction efficiency to be significantly dependent on pH, and suggested optimum conditions to be moderate temperatures and pH 8.5-9. Discussion of the practical convenience of these theoretical results led us to prefer 40-50 °C and a pH range of 7-8 as reaction conditions, thus maintaining reaction times within a few hours. Various N-carbamoyl amino acids (ureido derivatives of glycine, L-valine, L-alanine, L-leucine, DL-methionine, Nε-trifluoroacetyl-L-lysine, β-alanine) were thus successfully synthesised on the gram to kilogram scales.