ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate

Base Information

• Chemical Name: ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate
• CAS No.: 1057651-37-2
• Molecular Formula: C₂₂H₃₂N₂O₆
• Molecular Weight: 420.506
• Mol file: 1057651-37-2.mol

Synonyms:ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate

Chemical Property of ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate

There total 11 articles about ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 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:

ethyl (1R,3S,4S)-3-((tert-butoxycarbonyl)amino)-4-((methylsulfonyl)oxy)cyclohexane-1-carboxylate (1255529-31-7) + benzyl chloroformate (501-53-1,94274-21-2) → ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate (1057651-37-2)

Guidance literature:

ethyl (1R,3S,4S)-3-((tert-butoxycarbonyl)amino)-4-((methylsulfonyl)oxy)cyclohexane-1-carboxylate; With 1-Methyl-4-piperidone; sodium azide; at 80 ℃; for 15h;

With hydrogen; palladium 10% on activated carbon; In ethanol; ethyl acetate; at 20 ℃; for 0.666667h;

benzyl chloroformate; With sodium hydrogencarbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

Reference yield:

C14H26N2O4 (1210348-23-4) + benzyl chloroformate (501-53-1,94274-21-2) → ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate (1057651-37-2)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate; at 0 - 20 ℃;

DOI:10.1016/j.tet.2017.01.021

Reference yield:

(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one (119719-61-8) → ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate (1057651-37-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / 2 h / 90 °C / Reflux

1.2: 2 h / 80 °C

2.1: triethylamine; trimethylamine hydrochloride / ethyl acetate / 1 h / 0 °C

3.1: sodium azide; 1-Methyl-4-piperidone / 15 h / 80 °C

3.2: 0.67 h / 20 °C

3.3: 0.5 h / 0 °C

With 1-Methyl-4-piperidone; sodium azide; trimethylamine hydrochloride; potassium carbonate; triethylamine; In ethyl acetate;

upstream raw materials:

ethyl (1R,3S,4S)-3-((tert-butoxycarbonyl)amino)-4-((methylsulfonyl)oxy)cyclohexane-1-carboxylate

benzyl chloroformate

(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one

ethyl (1R,3S,4S)-3-((tert-butoxycarbonyl)amino)-4-hydroxycyclohexane-1-carboxylate