2717-75-1

Basic information

• Product Name: Tryptophan, N-benzoyl-, methyl ester (7CI)
• Synonyms: Tryptophan, N-benzoyl-, methyl ester (7CI)
• CAS NO: 2717-75-1
• Molecular Formula: C₁₉H₁₈N₂O₃
• Molecular Weight: 322.36
• Mol File: 2717-75-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 604.8°Cat760mmHg
• Flash Point: 319.6°C
• Appearance: /
• Density: 1.257g/cm³
• Vapor Pressure: 1.4E-14mmHg at 25°C
• Refractive Index: 1.639
• PKA: 13.12±0.46(Predicted)
• CAS DataBase Reference: Tryptophan, N-benzoyl-, methyl ester (7CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Tryptophan, N-benzoyl-, methyl ester (7CI)(2717-75-1)
• EPA Substance Registry System: Tryptophan, N-benzoyl-, methyl ester (7CI)(2717-75-1)

Safety Data

• Hazardous Substances Data: 2717-75-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H18N2O3/c1-24-19(23)17(21-18(22)13-7-3-2-4-8-13)11-14-12-20-16-10-6-5-9-15(14)16/h2-10,12,17,20H,11H2,1H3,(H,21,22)/t17-/m0/s1

Upstream product

• 120-72-9 indole 
• 126577-61-5 (S)-1-Benzoyl-aziridine-2-carboxylic acid methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 98-88-4 benzoyl chloride 
• 195727-70-9 1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine 
• 100-63-0 phenylhydrazine 
• 67-56-1 methanol 
• 253170-53-5 2-benzoylamino-3-(1H-indol-3-yl)-propionic acid 2,5,8,11,14,20,23,26,29,32-decaoxa-tricyclo[31.3.1.1^15,19]octatriaconta-1⁽³⁷⁾,15,17,19⁽³⁸⁾,33,35-hexaen-17-ylmethyl ester 
• 101693-51-0 4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one 
• 35737-15-6 Fmoc-Trp-OH 
• 253170-44-4 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-indol-3-yl)-propionic acid 2,5,8,11,14,20,23,26,29,32-decaoxa-tricyclo[31.3.1.1^15,19]octatriaconta-1⁽³⁷⁾,15,17,19⁽³⁸⁾,33,35-hexaen-17-ylmethyl ester 
• 2901-79-3 N-benzoyl-L-tryptophane 
• 4299-70-1 L-tryptophan methyl ester 
• 65-85-0 benzoic acid 

Downstream Products

• 55-21-0 benzamide 
• 82933-21-9 N-benzoyl-L-aspartic acid α-methyl ester 
• 137196-98-6 (R)-2-Benzoylamino-3-{2-[3-((S)-2-benzoylamino-2-methoxycarbonyl-ethyl)-1H-indol-2-yldisulfanyl]-1H-indol-3-yl}-propionic acid methyl ester 
• 85239-37-8 (S)-3-(1H-Indol-3-yl)-2-thiobenzoylamino-propionic acid methyl ester 
• 4299-70-1 L-tryptophan methyl ester 
• 2824-57-9 N-acetyl-L-tryptophan methyl ester 
• 73053-87-9 3-(2-phenyl-4-carbomethoxy-5-oxazolyl)indole 
• 79659-76-0 methyl N-benzoyl-1-methyl-L-tryptophanate 
• 104331-05-7 rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester 
• 863658-61-1 1-benzoyl-1,2,3,8-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester 
• 863658-62-2 (S)-1-Benzoyl-3a-((E)-3,7-dimethyl-octa-2,6-dienyl)-1,2,3,3a-tetrahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester 
• 863658-67-7 (2S,3aR,8aR)-3a-((E)-3,7-Dimethyl-octa-2,6-dienyl)-1-[(S)-3-phenyl-2-(2-trimethylsilanyl-ethoxycarbonylamino)-propionyl]-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid methyl ester 
• 54774-15-1 (S)-(+)-methylthiocarbonyl tryptophan methyl ester 
• 85239-47-0 (S)-1-Phenyl-4,9-dihydro-3H-β-carboline-3-carboxylic acid methyl ester; hydriodide 

Relevant articles and documents

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

Diboron-Catalyzed Dehydrative Amidation of Aromatic Carboxylic Acids with Amines

Tetrakis(dimethylamido)diboron and tetrahydroxydiboron are herein reported as new catalysts for the synthesis of aryl amides by catalytic condensation of aromatic carboxylic acids with amines. The developed protocol is both simple and highly efficient over a broad range of substrates. This method thus represents an attractive approach for the use of diboron catalysts in the synthesis of amides without having to resort to stoichiometric or additional dehydrating agents.

Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.