4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic Acid

Base Information

• Chemical Name: 4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic Acid
• CAS No.: 252206-28-3
• Molecular Formula: C₂₀H₁₇N₃O₄
• Molecular Weight: 363.373
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID50426690
• Nikkaji Number: J1.627.819J
• Wikidata: Q82239519
• Mol file: 252206-28-3.mol

Synonyms:252206-28-3;4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic Acid;4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-methylimidazole-2-carboxylic acid;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid;4-({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID;4-(9H-Fluoren-9-ylmethoxycarbonylamino)-1-methyl-1H-imidazole-2-carboxylic acid;SCHEMBL1577609;AMY6623;DTXSID50426690;AFUJLUWSTBUALR-UHFFFAOYSA-N;MFCD02259498;AKOS015896190;AC-8728;AS-37748;CS-0044529;FT-0659594;EN300-321718;A817716;A1-24395;J-015877;4-(Fmoc-amino)-1-methyl-1H-imidazole-2-carboxylic acid, AldrichCPR;4-[(9-florenylmethoxycarbonyl)amino]-1-methyl-2-imidazole carboxylic acid;1-Methyl-4-(9H-fluorene-9-ylmethoxycarbonylamino)-1H-imidazole-2-carboxylic acid;1H-Imidazole-2-carboxylic acid, 4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1-methyl-;4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylicacid;4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-methyl-imidazole-2-carboxylic acid

Chemical Property of 4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic Acid

Chemical Property:

• Refractive Index: 1.687
• PKA: 1.19±0.32(Predicted)
• PSA: 93.45000
• Density: 1.4g/cm³
• LogP: 3.55230
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 363.12190603
• Heavy Atom Count: 27
• Complexity: 549

Purity/Quality:

≥99.0% ^*data from raw suppliers

4-(FMOC-AMINO)-1-METHYL-1H-IMIDAZOLE-2-CARBOXYLIC ACID 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(N=C1C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of 4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic Acid

There total 10 articles about 4-(Fmoc-amino)-1-methyl-1H-Imidazole-2-carboxylic 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: 91.0%

benzyl 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1Himidazole-2-carboxylate → 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid (252206-28-3)

Guidance literature:

With palladium 10% on activated carbon; In tetrahydrofuran; at 20 ℃; for 4.5h;

DOI:10.1021/acs.orglett.9b04288

Reference yield: 86.0%

tert-butyl 4-[(9-fluorenylmethoxycarbonyl)amino]-N-methyl-1H-imidazole-2-carboxylate → 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid (252206-28-3)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol0156796

Reference yield:

2-trichloroacetyl-1-methylimidazole (30148-23-3) → 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid (252206-28-3)

Guidance literature:

Multi-step reaction with 5 steps

1: nitric acid; sulfuric acid; acetic anhydride / 0 - 20 °C / Large scale; Green chemistry

2: tert-butyl alcohol / 4 h / Reflux; Large scale

3: palladium on activated charcoal; hydrogen / methanol / 6 h / 85 °C

4: sodium hydrogencarbonate / 1,4-dioxane / 10 - 20 °C

5: sulfuric acid / dichloromethane / -5 - 30 °C / Inert atmosphere; Large scale

With sulfuric acid; palladium on activated charcoal; hydrogen; nitric acid; acetic anhydride; sodium hydrogencarbonate; In 1,4-dioxane; methanol; dichloromethane; tert-butyl alcohol;

upstream raw materials:

2-trichloroacetyl-1-methylimidazole

2,2,2-trichloro-1-(1-methyl-4-nitro-1H-imidazol-2-yl)ethan-1-one

tert-butyl 4-nitro-N-methyl-1H-imidazole-2-carboxylate

methyl 4-amino-1-methyl-1H-imidazole-2-carboxylate

Downstream raw materials:

4-amino-1-methyl-1H-imidazole-2-carboxylic acid

Refernces

• 1、 -. "Series of oligopolyamide containing N-methylpyrrole and N-methylimidazole and synthesis method thereof". Paragraph 0072; 0139-0142. . Retrieved 2019/10/02.