(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt

Base Information

• Chemical Name: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt
• CAS No.: 1383814-57-0
• Molecular Formula: C₆H₁₃N*C₁₄H₁₆N₂O₄
• Molecular Weight: 375.468
• Mol file: 1383814-57-0.mol

Synonyms:(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt

Chemical Property of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt

There total 12 articles about (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt 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: 86.0%

(2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate (1383814-56-9) + cyclohexylamine (108-91-8,157973-60-9) → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt (1383814-57-0)

Guidance literature:

tert-butyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]-octane-2-carboxylate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

cyclohexylamine; In diethyl ether; dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield:

(2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester (147489-30-3) → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt (1383814-57-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ethanol; sodium tetrahydroborate / 0.33 h / Cooling with ice

2.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 1.5 h / 20 °C / Inert atmosphere

3.1: triethylamine / tetrahydrofuran / 1.5 h / -5 - -3 °C / Inert atmosphere

4.1: trifluoromethylsulfonic anhydride; 2,6-dimethylpyridine / acetonitrile / 0.42 h / -40 - -30 °C / Inert atmosphere

4.2: 84.5 h / -30 - 5 °C

5.1: sodium hydroxide / 1,4-dioxane / 0.5 h / Cooling with ice

6.1: triethylamine / acetonitrile / 0.25 h / 0 °C / Inert atmosphere

6.2: 3 h / 0 - 20 °C

7.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

7.2: 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; ethanol; trifluoromethylsulfonic anhydride; hydrogen; triethylamine; trifluoroacetic acid; sodium hydroxide; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; acetonitrile;

Reference yield:

(S)-tert-butyl 2-(benzyloxycarbonylamino)-5-oxo-6-dimethylsulfoxonium hexanoate → (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid cyclohexylamine salt (1383814-57-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride / 1,2-dichloro-ethane / 2 h / 70 °C / Inert atmosphere

2.1: ethanol; sodium tetrahydroborate / 0.33 h / Cooling with ice

3.1: hydrogen / palladium 10% on activated carbon / ethanol; water / 1.5 h / 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 1.5 h / -5 - -3 °C / Inert atmosphere

5.1: trifluoromethylsulfonic anhydride; 2,6-dimethylpyridine / acetonitrile / 0.42 h / -40 - -30 °C / Inert atmosphere

5.2: 84.5 h / -30 - 5 °C

6.1: sodium hydroxide / 1,4-dioxane / 0.5 h / Cooling with ice

7.1: triethylamine / acetonitrile / 0.25 h / 0 °C / Inert atmosphere

7.2: 3 h / 0 - 20 °C

8.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

8.2: 1 h / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; ethanol; trifluoromethylsulfonic anhydride; hydrogen; triethylamine; trifluoroacetic acid; sodium hydroxide; bis(1,5-cyclooctadiene)diiridium(I) dichloride; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

upstream raw materials:

(2S,5R)-tert-butyl 5-(benzyloxyamino)piperidine-2-carboxylate

(2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate

cyclohexylamine

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate

Downstream raw materials:

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid benzyl ester

(2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid 2,5-dioxopyrrolidin-1-yl ester

(2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt

RG₆₀₈₀