ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate

Base Information

• Chemical Name: ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate
• CAS No.: 1193687-88-5
• Molecular Formula: C₂₀H₂₃FN₄O₆
• Molecular Weight: 434.424
• Mol file: 1193687-88-5.mol

Synonyms:ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate

Chemical Property of ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate

Chemical Property:

Purity/Quality:

>95% ^*data from raw suppliers

Ethyl2-[[1-[4-[[[(4-fluorophenyl)methyl]amino]carbonyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-2-pyrimidinyl]-1-methylethyl]amino]-2-oxoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Ethyl 2-[[1-[4-[[[(4-fluorophenyl)methyl]amino]carbonyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-2-pyrimidinyl]-1-methylethyl]amino]-2-oxoacetate, is an impurity of Raltegravir Potassium (R100300), a potent human immunodeficiency virus (HIV) integrase inhibitor. A novel anti-AIDS drug.

Technology Process of ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate

There total 5 articles about ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate 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: 89.0%

C17H20FN3O3 + Ethyl oxalyl chloride (4755-77-5) → ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate (1193687-88-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; Inert atmosphere;

DOI:10.1021/op300077m

Reference yield:

2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide (518048-03-8) + Ethyl oxalyl chloride (4755-77-5) → ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate (1193687-88-5)

Guidance literature:

With triethylamine; In chloroform; at 0 - 20 ℃; for 2.5h;

DOI:10.14233/ajchem.2019.22246

Reference yield:

2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester (888504-27-6) → ethyl (2-(4-(4-fluorobenzylcarbamoyl)-1,6-dihydro-5-hydroxy-1-methyl-6-oxopyrimidin-2-yl)propan-2-ylcarbamoyl)formate (1193687-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / 3 h / Reflux

2: sodium hydroxide / ethanol; butan-1-ol / Reflux

3: triethylamine / chloroform / 2.5 h / 0 - 20 °C

With triethylamine; sodium hydroxide; In ethanol; chloroform; butan-1-ol;

DOI:10.14233/ajchem.2019.22246

upstream raw materials:

Ethyl oxalyl chloride

2-(1-amino-1-methyl-ethyl)-N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-4-pyrimidinecarboxamide

2-(1-benzyloxycarbonylamino-1-methyl-ethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid methyl ester

para-fluorobenzylamine

Downstream raw materials:

raltegravir

C₁₈H₂₀FN₅O₅

Refernces

• 1、 Patil, Gulabrao D.,Kshirsagar, Siddheshwar W.,Shinde, Shivnath B.,Patil, Pankaj S.,Deshpande, Mangesh S.,Chaudhari, Ashok T.,Sonawane, Swapnil P.,Maikap, Golak C.,Gurjar, Mukund K.. "Identification, synthesis, and strategy for minimization of potential impurities observed in raltegravir potassium drug substance". . p. 1422 - 1429. Retrieved 2012/10/29.