(4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester
• CAS No.: 1609349-56-5
• Molecular Formula: C₂₅H₂₉F₃N₂O₅
• Molecular Weight: 494.511
• Mol file: 1609349-56-5.mol

Synonyms:(4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester

Chemical Property of (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester

There total 8 articles about (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester 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:

4-(benzyloxy)benzoic acid chloride (1486-50-6) + C11H19F3N2O3 (1609349-57-6) → (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester (1609349-56-5)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1002/ejoc.201301811

Reference yield:

tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-1-carboxylate (1609349-55-4) → (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester (1609349-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluorormethanesulfonic acid; hydrogen; 5%-palladium/activated carbon / methanol / 14 h

2: triethylamine / dichloromethane / 2 h / 25 °C

With trifluorormethanesulfonic acid; 5%-palladium/activated carbon; hydrogen; triethylamine; In methanol; dichloromethane;

DOI:10.1002/ejoc.201301811

Reference yield:

tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylate (1609349-53-2) → (4R,5S,6R)-6-(4-(benzyloxy)benzamido)-3,3,4-trifluoro-5-hydroxyazepane-1-carboxylic acid tert-butyl ester (1609349-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium chlorochromate / dichloromethane / 25 °C / Inert atmosphere; Molecular sieve

2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / 10 h / 0 °C / Inert atmosphere

3: trifluorormethanesulfonic acid; hydrogen; 5%-palladium/activated carbon / methanol / 14 h

4: triethylamine / dichloromethane / 2 h / 25 °C

With trifluorormethanesulfonic acid; 5%-palladium/activated carbon; hydrogen; triethylamine; pyridinium chlorochromate; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In methanol; dichloromethane;

DOI:10.1002/ejoc.201301811

upstream raw materials:

tert-butyl (3R,4S,5S,6R)-3-azido-4-benzyloxy-5-fluoro-6-hydroxyazepane-1-carboxylate

tert-butyl (3R,4S,5R)-3-azido-4-benzyloxy-5-fluoro-6-oxoazepane-1-carboxylate

tert-butyl (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepane-1-carboxylate

4-(benzyloxy)benzoic acid chloride