methyl 2-benzamido-3-(1H-imidazol-5-yl)propanoate

Base Information

• Chemical Name: methyl 2-benzamido-3-(1H-imidazol-5-yl)propanoate
• CAS No.: 3005-62-7
• Molecular Formula: C14H15N3O3
• Molecular Weight: 273.291
• Hs Code.: 2933290090
• NSC Number: 164028
• DSSTox Substance ID: DTXSID50304040
• Mol file: 3005-62-7.mol

Synonyms:methyl 2-benzamido-3-(1H-imidazol-5-yl)propanoate;Bz-L-His-OMe;NSC164028;Histidine, derivative of;DTXSID50304040;NSC-164028

Chemical Property of methyl 2-benzamido-3-(1H-imidazol-5-yl)propanoate

Chemical Property:

• Vapor Pressure: 1.97E-14mmHg at 25°C
• Refractive Index: 1.588
• Boiling Point: 601.7 °C at 760 mmHg
• Flash Point: 317.7 °C
• PSA: 84.08000
• Density: 1.268 g/cm³
• LogP: 1.31470
• Storage Temp.: Store at RT.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 273.11134135
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

99% ^*data from raw suppliers

N-alpha-Benzoyl-L-histidine methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CN=CN1)NC(=O)C2=CC=CC=C2

Technology Process of methyl 2-benzamido-3-(1H-imidazol-5-yl)propanoate

There total 13 articles about methyl 2-benzamido-3-(1H-imidazol-5-yl)propanoate 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: 71.0%

histidine methyl ester hydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) + benzoyl chloride (98-88-4) → (S)-(-)-methyl 2-benzamido-3-(4,5-dihydro-1H-imidazol-5-yl)propanoate (3005-62-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.molliq.2014.10.028

Reference yield: 21.0%

benzoyl chloride (98-88-4) + l-histidine methyl ester dihydrochloride (4467-54-3,5619-10-3,7389-87-9,18684-16-7,22888-60-4,32381-17-2,92742-29-5,100009-20-9) → (S)-(-)-methyl 2-benzamido-3-(4,5-dihydro-1H-imidazol-5-yl)propanoate (3005-62-7)

Guidance literature:

With TEA; In chloroform; at 20 ℃; for 48h;

DOI:10.1016/j.tetasy.2007.12.013

Reference yield:

chloroform (67-66-3,8013-54-5) + furan-2,3,5(4H)-trione pyridine (1:1) + glycine (56-40-6,18875-39-3,25718-94-9) → N-acetylglycine (543-24-8) + (S)-(-)-methyl 2-benzamido-3-(4,5-dihydro-1H-imidazol-5-yl)propanoate (3005-62-7)

Guidance literature:

at 25 ℃; bei der Reaktion mit 1-Benzoyl-theobromin erhaelt man analog Hippursaeure und Theobromin;

upstream raw materials:

methanol

N-benzoyl-L-histidine

N^α-benzoyl-N^Im-tosyl-L-histidine methyl ester

1,N^α-dibenzoyl-histidine methyl ester

Downstream raw materials:

N(α)-benzoyl-N(τ)-(2-acetoxyethyl)histidine methyl ester

N(α)-benzoyl-N(τ)-(2-benzyloxyethyl)histidine methyl ester

(S,αS)-N^α-benzoyl-N^τ-(2-hydroxypropyl)-L-histidine methyl ester

(S,αS)-N^α-benzoyl-N^?-(2-hydroxypropyl)-L-histidine methyl ester

Refernces

• 1、 Yuvaraj, Surya V.J.,Subbotin, Oleg S.,Belosludov, Rodion V.,Belosludov, Vladimir R.,Kanie, Kiyoshi,Funaki, Kenji,Muramatsu, Atsushi,Nakamura, Takashi,Mizuseki, Hiroshi,Kawazoe, Yoshiyuki. "Theoretical evaluation on solubility of synthesized task specific ionic liquids in water". . p. 232 - 237. Retrieved 2015/02/19.
• 2、 Campbell, John B.. "The Synthesis of N(τ)-(2-hydroxypropyl)histidine, N(τ)-2-hydroxyethyl)histidine, and Their Deuteriated Analogues". . p. 1213 - 1218. Retrieved 2007/10/02.