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

Base Information

• Chemical Name: (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one
• CAS No.: 1471297-60-5
• Molecular Formula: C₁₅H₁₇N₅O₃
• Molecular Weight: 315.332
• Mol file: 1471297-60-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one 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: 7.0%

(E)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde oxime + guanidine hydrochloride (50-01-1) → (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one (1471297-60-5)

Guidance literature:

(E)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde oxime; With pyridine; N-chloro-succinimide; In dichloromethane; at 20 ℃; for 18h;

guanidine hydrochloride; With sodium ethanolate; In ethanol; at 20 ℃;

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one (1471297-60-5)

Guidance literature:

Multi-step reaction with 11 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 borohydride; methanol / -10 - 0 °C

9.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 2 h / 0 °C

10.1: pyridine; hydroxylamine hydrochloride / ethanol / 2 h / 20 °C

11.1: pyridine; N-chloro-succinimide / dichloromethane / 18 h / 20 °C

11.2: 20 °C

With pyridine; methanol; dirhodium tetraacetate; sodium tetrahydroborate; N-chloro-succinimide; lithium borohydride; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium hydroxide monohydrate; ethanol; trichloroisocyanuric acid; hydroxylamine hydrochloride; mercaptoacetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 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) → (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one (1471297-60-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium borohydride; methanol / -10 - 0 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid / dichloromethane / 2 h / 0 °C

3.1: pyridine; hydroxylamine hydrochloride / ethanol / 2 h / 20 °C

4.1: pyridine; N-chloro-succinimide / dichloromethane / 18 h / 20 °C

4.2: 20 °C

With pyridine; methanol; N-chloro-succinimide; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; hydroxylamine hydrochloride; In ethanol; dichloromethane;

upstream raw materials:

guanidine hydrochloride

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

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

(S)-ethyl N-tert-butoxycarbonylpyroglutamate