(R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide

Base Information

• Chemical Name: (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide
• CAS No.: 1068148-44-6
• Molecular Formula: C₃₆H₄₇N₅O₅
• Molecular Weight: 629.8
• Mol file: 1068148-44-6.mol

Synonyms:(R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide

Chemical Property of (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide

There total 5 articles about (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide 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: 81.0%

N-benzyloxycarbonyl-N'-tert-butoxycarbonyl-1H-pyrazole-1-carboxamidine + (R)-N'-(4-tert-butoxybenzyl)-Nα-(2,2-diphenylacetyl)ornithinamide (1093677-53-2) → (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide (1068148-44-6)

Guidance literature:

N-benzyloxycarbonyl-N'-tert-butoxycarbonyl-1H-pyrazole-1-carboxamidine; (R)-N'-(4-tert-butoxybenzyl)-N^α-(2,2-diphenylacetyl)ornithinamide; With diethylamine; In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 20h;

DOI:10.1071/CH15569

Reference yield:

C44H53N5O7 → (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide (1068148-44-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/jm801018u

Reference yield:

Nε-(benzyloxycarbonyl)ornithine (16937-91-0,118578-06-6) → (R)-N-(4-tert-butoxybenzyl)-Nω-tert-butoxycarbonyl-Nα-(2,2-diphenylacetyl)argininamide (1068148-44-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium carbonate / 1,4-dioxane; water / 20 h / 50 °C

2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.5 h

2.2: 20 h / 20 °C / Inert atmosphere

3.1: ammonium formate; palladium on activated charcoal / methanol / 20 h / 20 °C

4.1: diethylamine / dichloromethane / 20 h / 20 °C / Inert atmosphere

4.2: 20 h / 20 °C

With palladium on activated charcoal; ammonium formate; sodium carbonate; diethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1071/CH15569

upstream raw materials:

(R)-N'-(4-tert-butoxybenzyl)-N^α-(2,2-diphenylacetyl)ornithinamide

N^ε-(benzyloxycarbonyl)ornithine

succinimidyl 2,2-diphenylacetate

Refernces

• 1、 Keller, Max,Pop, Nathalie,Hutzler, Christoph,Beck-Sickinger, Annette G.,Bernhardt, Günther,Buschauer, Armin. "Guanidine-acylguanidine bioisosteric approach in the design of radioligands: Synthesis of a tritium-labeled NG-propionylargininamide ([3H]-UR-MK114) as a highly potent and selective neuropeptide Y Y1 receptor antagonist". supporting information; experimental part. p. 8168 - 8172. Retrieved 2009/12/07.