(R)-methyl 2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride

Base Information

• Chemical Name: (R)-methyl 2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride
• CAS No.: 4467-54-3
• Molecular Formula: C7H11N3O2^.2(HCl)
• Molecular Weight: 242.10
• Hs Code.: 29224919
• European Community (EC) Number: 680-160-1
• DSSTox Substance ID: DTXSID40505928
• Mol file: 4467-54-3.mol

Synonyms:4467-54-3;(R)-methyl 2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride;D-Histidine Methyl Ester Dihydrochloride;H-D-His-OMe.2HCl;methyl d-histidinate dihydrochloride;(R)-Methyl 2-amino-3-(1h-imidazol-5-yl)propanoate 2hcl;methyl (2R)-2-amino-3-(1H-imidazol-5-yl)propanoate;dihydrochloride;H-D-His-OMe-2HCl;D-HISTIDINE METHYLESTER DIHYDROCHLORIDE;H-D-His-ome dihydrochloride;D-Histidine methyl ester 2HCl;SCHEMBL9081237;DTXSID40505928;DWAYENIPKPKKMV-QYCVXMPOSA-N;MFCD00066137;AKOS015845182;AKOS015898175;FD21661;FS-4068;H-D-His-OMe dihydrochloride, AldrichCPR;AM20100151;CS-0127698;H1213;EN300-716368;Methyl D-histidinate--hydrogen chloride (1/2);A872481;Z2943587888;(R)-Methyl 2-amino-3-(1h-imidazol-5-yl)propanoate dihydrochloride;(R)-methyl2-amino-3-(1H-imidazol-4-yl)propanoatedihydrochloride;methyl (2R)-2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride

Chemical Property of (R)-methyl 2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride

Chemical Property:

• Vapor Pressure: 2.67E-07mmHg at 25°C
• Melting Point: 197oC
• Refractive Index: -9.0 ° (C=2, H2O)
• Boiling Point: 415.4 °C at 760 mmHg
• Flash Point: 205 °C
• PSA: 81.00000
• LogP: 0.95480
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 241.0384821
• Heavy Atom Count: 14
• Complexity: 163

Purity/Quality:

98%,99%, ^*data from raw suppliers

D-HistidineMethylEsterHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34-36/37/38
• Safety Statements: 26-36/37/39-43-45-60-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CN=CN1)N.Cl.Cl
• Isomeric SMILES: COC(=O)[C@@H](CC1=CN=CN1)N.Cl.Cl
• Uses: D-Histidine methyl ester is a protected form of D-Histidine (H456015). D-Histidine is the unnatural, biologically inactive isomer of L-Histidine (H456010). D-histidine is known to inhibit cell division, and is also used by certain types of bacteria (such as Escherichia coli) as a source of L-Histidine.

Technology Process of (R)-methyl 2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride

There total 20 articles about (R)-methyl 2-amino-3-(1H-imidazol-4-yl)propanoate dihydrochloride 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: 100.0%

L-histidine monohydrochloride (645-35-2) + trimethyl orthoformate (149-73-5) → 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)

Guidance literature:

With thionyl chloride; In methanol; at 0 ℃; for 16h; Inert atmosphere; Reflux;

DOI:10.1002/chir.22056

Reference yield: 100.0%

methanol (67-56-1) + L-histidine (71-00-1,26062-48-6,90081-11-1) → 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)

Guidance literature:

With acetyl chloride; for 24h;

DOI:10.1002/chem.200601420

Reference yield: 100.0%

D-histidine monohydrochloride (6341-24-8) + trimethyl orthoformate (149-73-5) → (R)-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)

Guidance literature:

With thionyl chloride; In methanol; at 0 ℃; for 16h; Inert atmosphere; Reflux;

DOI:10.1002/chir.22056

upstream raw materials:

methanol

L-histidine

D-histidine

L-histidine

Downstream raw materials:

methyl N-(diphenylmethylene)-L-histidinate

Z-glycyl-glycyl-L-histidine methyl ester

Benzyloxycarbonyl-Val-His-OMe

Benzyloxycarbonyl-Leu-His-OMe

Refernces

• 1、 Torikai, Kohei,Watanabe, Louis A.,Yanagimoto, Ryota. "N(?)-2-Naphthylmethoxymethyl-Protected Histidines: Scalable, Racemization-Free Building Blocks for Peptide Synthesis". . p. 448 - 453. Retrieved 2020/04/08.
• 2、 Sotgia, Salvatore,Murphy, Rhys B.,Zinellu, Angelo,Elliot, David,Paliogiannis, Panagiotis,Pinna, Gerard Aimè,Carru, Ciriaco,Mangoni, Arduino A.. "Development of an LC–tandem mass spectrometry method for the quantitative analysis of hercynine in human whole blood". supporting information. . Retrieved 2019/01/03.