2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide

Base Information

• Chemical Name: 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide
• CAS No.: 147269-75-8
• Molecular Formula: C₃₀H₃₂F₃N₃O₇
• Molecular Weight: 603.595
• Mol file: 147269-75-8.mol

Synonyms:2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide

Chemical Property of 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide

There total 10 articles about 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide 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: 90.0%

2-[3-benzyloxycarbonylamino-5-(4-methoxycarbonylbenzyl)-2-oxo-1,2-dihydro-1-pyridyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (147269-74-7) → 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (147269-75-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.25h;

DOI:10.1021/jm00045a014

Reference yield:

3-nitropyridone (6332-56-5) → 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (147269-75-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / H₂ / 10percent Pd/C / ethanol / 8 h / 760 Torr / Ambient temperature

2: 63 percent / Na₂CO₃ / tetrahydrofuran

3: 46 percent / N-iodosuccinimide / CH₂Cl₂ / 18 h

4: 1.) NaH / 1.) DMF, 15-25 deg C, 20 min, 2.) DMF, RT, 3 h

5: 1.) Zn, 2.) dichloro<1,1'-bis(diphenylphosphino)ferrocene>palladium(II) / 1.) THF, 20 deg C, 3 h, 2.) THF, a) RT, 5 h, b) 50 deg C, 4.5 h, c) RT, 18 h

6: 90 percent / tetrabutylamminum fluoride / tetrahydrofuran / 0.25 h

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium carbonate; zinc; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm00045a014

Reference yield:

3(RS)-amino-1,1,1-trifluoro-2(RS)-hydroxy-4-methylpentane hydrochloride (106746-09-2) → 2-<3-<<(benzyloxy)carbonyl>amino>-5-<4-(methoxycarbonyl)benzyl>-2-oxo-1,2-dihydro-1-pyridyl>-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide (147269-75-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 4-methylmorpholine / tetrahydrofuran / 18 h

2: 2,6-lutidine / 12 h

3: 92 percent / NaI / acetone / 18 h

4: 1.) NaH / 1.) DMF, 15-25 deg C, 20 min, 2.) DMF, RT, 3 h

5: 1.) Zn, 2.) dichloro<1,1'-bis(diphenylphosphino)ferrocene>palladium(II) / 1.) THF, 20 deg C, 3 h, 2.) THF, a) RT, 5 h, b) 50 deg C, 4.5 h, c) RT, 18 h

6: 90 percent / tetrabutylamminum fluoride / tetrahydrofuran / 0.25 h

With 4-methyl-morpholine; 2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; zinc; In tetrahydrofuran; acetone;

DOI:10.1021/jm00045a014

upstream raw materials:

2-[3-benzyloxycarbonylamino-5-(4-methoxycarbonylbenzyl)-2-oxo-1,2-dihydro-1-pyridyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide

3-nitropyridone

3(RS)-amino-1,1,1-trifluoro-2(RS)-hydroxy-4-methylpentane hydrochloride

3-amino-2-pyridone