3-(1-Trityl-1H-imidazol-4-yl)propanoic acid

Base Information

• Chemical Name: 3-(1-Trityl-1H-imidazol-4-yl)propanoic acid
• CAS No.: 160446-35-5
• Molecular Formula: C25H22 N2 O2
• Molecular Weight: 382.462
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID30428612
• Mol file: 160446-35-5.mol

Synonyms:160446-35-5;3-(1-Trityl-1H-imidazol-4-yl)propanoic acid;3-(1-tritylimidazol-4-yl)propanoic Acid;Deamino-His(Trt)-OH;3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONIC ACID;N-1-TRITYL-DEAMINO-HISTIDINE;N-1-Trityl-deamino-histidine hydrochloride salt;N-1-Trityl-dihydrourocanic acid;3-(N-1-Trityl-imidazol-4-yl)-propionic acid;1H-Imidazole-4-propanoic acid, 1-(triphenylmethyl)-;Deamino-His(Trt)-OH.nHCl;SCHEMBL877785;DTXSID30428612;WPUNOGRJNPUUQT-UHFFFAOYSA-N;MFCD00237290;AKOS015901172;FD21698;3-(N-Tritylimidazol-4-yl)propionic acid;AS-49164;3-(1-trityl-1h-imidazol-4-yl)-propionic acid;3-(1-Triphenylmethyl-4-imidazolyl)propionic acid;1H-Imidazole-4-propanoicacid,1-(triphenylmethyl)-;3-(N-1-TRITYL-IMIDAZOL-4-YL)PROPIONICACID;3-[1-(triphenylmethyl)-1H-imidazol-4-yl]propanoic acid;N-1-Trityl-deamino-histidine, (3-(N-1-Trityl-imidazol-4-yl)propionic acid, N-1-Trityl-dihydrourocanic acid

Chemical Property of 3-(1-Trityl-1H-imidazol-4-yl)propanoic acid

Chemical Property:

• Melting Point: 185℃ (ethyl acetate tetrahydrofuran )
• Boiling Point: 562.8±45.0 °C(Predicted)
• PKA: 3.94±0.10(Predicted)
• PSA: 55.12000
• Density: 1.13±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 4.74050
• Storage Temp.: -15°C
• Solubility.: Chloroform (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 382.168127949
• Heavy Atom Count: 29
• Complexity: 473

Purity/Quality:

99% ^*data from raw suppliers

3-(N-1-Trityl-imidazol-4-yl)propionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)N4C=C(N=C4)CCC(=O)O
• Uses: 3-(N-1-Trityl-imidazol-4-yl)propionic Acid is an intermediate used to prepare imidazole-containing tetrahydrobenzodiazepine inhibitors of farnesyltransferase. It is also used in the synthesis of nonracemic arylpiperazinone analogs of the carboxyl-terminal CAAL sequence of protein geranylgeranyltransferase-I (PGGTase-I) as selective inhibitors of PGGTase-I and of protein farnesyltransferase.

Technology Process of 3-(1-Trityl-1H-imidazol-4-yl)propanoic acid

There total 12 articles about 3-(1-Trityl-1H-imidazol-4-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: 97.0%

3-(1-triphenylmethyl-1H-imidazol-4-yl)propanoic acid methyl ester (102676-60-8) → 3-(1H-1-triphenylmethylimidazol-4-yl)propanoic acid (160446-35-5)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 23 ℃; Large scale;

Reference yield: 76.0%

(E)-3-(1-trityl-1H-imidazol-4-yl)acrylic acid (125872-93-7) → 3-(1H-1-triphenylmethylimidazol-4-yl)propanoic acid (160446-35-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1021/jm0309147

Reference yield:

trityl chloride (76-83-5) + 3-(imidazol-4-yl)propionic acid (1074-59-5) → 3-(1H-1-triphenylmethylimidazol-4-yl)propanoic acid (160446-35-5)

Guidance literature:

With chloro-trimethyl-silane; triethylamine; In methanol; dichloromethane; water; acetonitrile;

upstream raw materials:

3-(1-triphenylmethyl-1H-imidazol-4-yl)propanoic acid methyl ester

(E)-3-(1-trityl-1H-imidazol-4-yl)acrylic acid

3-(4-imidazolyl)propionic acid monohydrochloride

trityl chloride

Downstream raw materials:

N-[2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethyl]-3-(1-trityl-1H-imidazol-4-yl)propionamide

C₅₈H₆₀N₄O₄

C₅₈H₆₀N₄O₄

C₅₈H₆₀N₄O₄

Refernces

• 1、 Ghorai, Prasanta,Kraus, Anja,Keller, Max,G?tte, Carsten,Igel, Patrick,Schneider, Erich,Schnell, David,Bernhardt, Günther,Dove, Stefan,Zabel, Manfred,Elz, Sigurd,Seifert, Roland,Buschauer, Armin. "Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine h2 receptor agonists". supporting information; experimental part. p. 7193 - 7204. Retrieved 2009/10/02.
• 2、 Menghin, Sonja,Pertz, Heinz H.,Kramer, Kai,Seifert, Roland,Schunack, Walter,Elz, Sigurd. "Nα-Imidazolylalkyl and Pyridylalkyl Derivatives of Histaprodifen: Synthesis and in Vitro Evaluation of Highly Potent Histamine H1-Receptor Agonists". . p. 5458 - 5470. Retrieved 2007/10/03.