tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate
• CAS No.: 1471298-12-0
• Molecular Formula: C₂₅H₃₃N₅O₅
• Molecular Weight: 483.568

Synonyms:tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

Chemical Property of tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

There total 12 articles about tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-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:

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (1174020-25-7,2064219-13-0) + (E)-tert-butyl 4-(N’-hydroxycarbamimidoyl)piperidine-1-carboxylate (1421065-40-8,280110-63-6,782493-60-1) → tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1471298-12-0)

Guidance literature:

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

(E)-tert-butyl 4-(N’-hydroxycarbamimidoyl)piperidine-1-carboxylate; In N,N-dimethyl-formamide; at 20 - 50 ℃; for 8h;

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1471298-12-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

1.2: 0.5 h / -78 °C

2.1: dirhodium tetraacetate / dichloromethane / 0 - 20 °C

3.1: sodium tetrahydroborate; ethanol / 0.5 h / -40 °C

4.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 °C

5.1: lithium hydroxide monohydrate; mercaptoacetic acid / N,N-dimethyl-formamide / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 20 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

8.1: lithium hydroxide; water / tetrahydrofuran / 20 °C

9.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 20 °C

9.2: 8 h / 20 - 50 °C

With dirhodium tetraacetate; sodium tetrahydroborate; n-butyllithium; lithium hydroxide monohydrate; ethanol; water; mercaptoacetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; lithium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester (1416134-63-8) → tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1471298-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydroxide; water / tetrahydrofuran / 20 °C

2.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 8 h / 20 - 50 °C

With water; 1,1'-carbonyldiimidazole; lithium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

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

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

(E)-tert-butyl 4-(N’-hydroxycarbamimidoyl)piperidine-1-carboxylate

ethyl (S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ⁶-sulfanylidene)-5-oxohexanoate

Downstream raw materials:

(9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

(2S,5R)-6-(benzyloxy)-2-(3-(piperidin-4-yl)-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one

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