(S)-Methyl 2-acetamido-3-(1H-imidazol-4-yl)propanoate

Base Information

• Chemical Name: (S)-Methyl 2-acetamido-3-(1H-imidazol-4-yl)propanoate
• CAS No.: 36097-48-0
• Molecular Formula: C9H13N3O3
• Molecular Weight: 211.22
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID401300849
• Nikkaji Number: J852.752K
• Mol file: 36097-48-0.mol

Synonyms:36097-48-0;(S)-Methyl 2-acetamido-3-(1H-imidazol-4-yl)propanoate;Acetyl-L-histidine methyl ester;N-Acetyl-L-histidine methyl ester;SCHEMBL5808669;FWHBBEZPJALIIF-QMMMGPOBSA-N;DTXSID401300849;MFCD00237490;AS-75895;CS-0199107;D97509;EN300-197381;A823126;(S)-Methyl2-acetamido-3-(1H-imidazol-4-yl)propanoate;methyl (2S)-2-acetamido-3-(1H-imidazol-4-yl)propanoate;methyl (2S)-2-acetamido-3-(1H-imidazol-5-yl)propanoate

Chemical Property of (S)-Methyl 2-acetamido-3-(1H-imidazol-4-yl)propanoate

Chemical Property:

• Vapor Pressure: 1.84E-10mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 508.5 °C at 760 mmHg
• Flash Point: 261.4 °C
• PSA: 84.08000
• Density: 1.245 g/cm³
• LogP: 0.02080
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 211.09569129
• Heavy Atom Count: 15
• Complexity: 245

Purity/Quality:

98%min ^*data from raw suppliers

N-Acetyl-L-histidineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CN=CN1)C(=O)OC
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CN=CN1)C(=O)OC
• Uses: N-Acetyl-L-histidine Methyl Ester is the N-acetylated methyl ester of L-Histidine (H456010), an essential amino acid.

Technology Process of (S)-Methyl 2-acetamido-3-(1H-imidazol-4-yl)propanoate

There total 12 articles about (S)-Methyl 2-acetamido-3-(1H-imidazol-4-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: 90.0%

methanol (67-56-1) + N-acetyl-L-histidine (2497-02-1) → Nα-acetyl-L-histidine methyl ester (36097-48-0)

Guidance literature:

With thionyl chloride; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2007.08.010

Reference yield:

L-histidine methyl ester hydrochloride + acetyl chloride (75-36-5) → N-acetyl-(S)-histidine methyl ester (36097-48-0)

Guidance literature:

L-histidine methyl ester hydrochloride; With triethylamine; In dichloromethane; at 0 ℃; for 0.25h; Schlenk technique;

acetyl chloride; In dichloromethane; at 0 - 20 ℃; for 12h; Schlenk technique;

DOI:10.1002/ejoc.201901572

Reference yield:

L-histidine (71-00-1,26062-48-6,90081-11-1) → N-acetyl-(S)-histidine methyl ester (36097-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / 0 - 20 °C / Schlenk technique

2.1: triethylamine / dichloromethane / 0.25 h / 0 °C / Schlenk technique

2.2: 12 h / 0 - 20 °C / Schlenk technique

With thionyl chloride; triethylamine; In dichloromethane;

DOI:10.1002/ejoc.201901572

upstream raw materials:

methanol

N-acetyl-L-histidine

L-histidine

(1R,2R)-N-acetyl-1,2-bis(trifluoromethanesulfonamido) cyclohexane

Downstream raw materials:

2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester

N-α-acetyl-2-(4-trifluoromethylphenyl)-L-histidine methyl ester

N-α-acetyl-2-(2-napthyl)-1-benzyl-L-histidine methyl ester

N-α-acetyl-2-biphenyl-1-benzyl-L-histidine methyl ester

Refernces

• 1、 Sch?del, Nicole,Icik, Esra,Martini, Maike,Altevogt, Luca,Ramming, Isabell,Greulich, Andreas,Baro, Angelika,Bilitewski, Ursula,Laschat, Sabine. "Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine". supporting information. p. 2260 - 2268. Retrieved 2021/03/04.
• 2、 Ding, Bo,Weng, Yue,Liu, Yunqing,Song, Chunlan,Yin, Le,Yuan, Jiafan,Ren, Yanrui,Lei, Aiwen,Chiang, Chien-Wei. "Selective Photoredox Trifluoromethylation of Tryptophan-Containing Peptides". . p. 7596 - 7605. Retrieved 2019/12/15.