2-benzamido-3-(1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: 2-benzamido-3-(1H-indol-3-yl)propanoic acid
• CAS No.: 4302-66-3
• Molecular Formula: C18H16N2O3
• Molecular Weight: 308.33
• Hs Code.: 2933990090
• NSC Number: 305271,164035
• DSSTox Substance ID: DTXSID30304043
• ChEMBL ID: CHEMBL1412132
• Mol file: 4302-66-3.mol

Synonyms:2-benzamido-3-(1H-indol-3-yl)propanoic acid;N-benzoyltryptophan;Bz-L-Trp-OH;55629-71-5;4302-66-3;N-Benzoyltryptamin;NSC305271;Cambridge id 5104989;N-(phenylcarbonyl)tryptophan;Oprea1_321767;CBDivE_001947;MLS000085143;MEGxm0_000360;SCHEMBL5259129;CHEMBL1412132;ACon0_001433;DTXSID30304043;WPBCXLCJWLNDPV-UHFFFAOYSA-N;HMS2421K11;NSC164035;STK030660;AKOS001661512;AKOS016050992;NSC-164035;NSC-305271;SMR000019683;EU-0014303;FT-0773523;2-(benzoylamino)-3-(indol-3-yl)propanoic acid;AB00073703-01

Chemical Property of 2-benzamido-3-(1H-indol-3-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 1.15E-17mmHg at 25°C
• Melting Point: 193-194 °C
• Refractive Index: 1.681
• Boiling Point: 647.8 °C at 760 mmHg
• PKA: 3.82±0.10(Predicted)
• Flash Point: 345.6 °C
• PSA: 82.19000
• Density: 1.335 g/cm³
• LogP: 2.98450
• Storage Temp.: Store at RT.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 308.11609238
• Heavy Atom Count: 23
• Complexity: 434

Purity/Quality:

99%, ^*data from raw suppliers

Bz-L-Trp-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O

Technology Process of 2-benzamido-3-(1H-indol-3-yl)propanoic acid

There total 18 articles about 2-benzamido-3-(1H-indol-3-yl)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

benzoyl chloride (98-88-4) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-benzoyl-L-tryptophane (2901-79-3,4302-66-3,55629-71-5)

Guidance literature:

L-Tryptophan; With sodium hydroxide; In water; Cooling with ice;

benzoyl chloride; In water; at 20 ℃; Cooling with ice;

DOI:10.1039/d0md00097c

Reference yield: 88.0%

N-benzoyl-L-tryptophan methyl ester (2717-75-1) → N-benzoyl-L-tryptophane (2901-79-3,4302-66-3,55629-71-5)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 50 ℃; for 4h;

DOI:10.1111/cbdd.13156

Reference yield:

2-(benzoylamino)-3-(indol-3-yl)propanoic acid (2901-79-3) → D-Nα-benzoyltryptophane (55629-71-5) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + N-benzoyl-L-tryptophane (2901-79-3,4302-66-3,55629-71-5)

Guidance literature:

With D-glucose; corn steep liquor; fungus Beauveria bassiana ATCC 7159; In ethanol; water; for 72h; Title compound not separated from byproducts; Enzymatic reaction;

DOI:10.1007/s007060070095

upstream raw materials:

benzoyl chloride

L-Tryptophan

4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one

benzoic acid N-hydroxysuccinimide ester

Downstream raw materials:

1-Benzoyl-3a-hydroxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid

2-Benzoylamino-4-(2-formylamino-phenyl)-4-oxo-butyric acid

4-(1H-indol-3-ylmethyl)-2-phenyl-4H-oxazolin-5-one

N-(N-benzoyl-L-tryptophanyl)-D-phenylalanine methyl ester

Refernces

• 1、 Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao. "Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors". . p. 893 - 901. Retrieved 2018/03/21.
• 2、 Paul, Saurav,Roy, Ashalata,Deka, Suman Jyoti,Panda, Subhankar,Srivastava, Gopal Narayan,Trivedi, Vishal,Manna, Debasis. "Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1". . p. 1640 - 1654. Retrieved 2017/08/22.