(2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Base Information

Chemical Name:(2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
CAS No.:1471297-86-5
Molecular Formula:C₁₇H₂₂N₄O₃
Molecular Weight:330.387
Hs Code.:

Synonyms:(2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

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Chemical Property of (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

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Technology Process of (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

There total 13 articles about (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 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: 80.0%

: 1192651-49-2
(1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 1471297-86-5
(2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Guidance literature:: In 1,4-dioxane; at 45 - 50 ℃; for 2h;

Reference yield:

: 144978-35-8,144978-12-1,251924-83-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate

: 1471297-86-5
(2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Guidance literature:: Multi-step reaction with 10 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: N-ethyl-N,N-diisopropylamine; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 17 h / 20 °C

10.1: 1,4-dioxane / 2 h / 45 - 50 °C

With dirhodium tetraacetate; sodium tetrahydroborate; n-butyllithium; lithium hydroxide monohydrate; ethanol; water; ammonium chloride; benzotriazol-1-ol; mercaptoacetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 1463501-45-2
(2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-(2-nitrophenyl)sulfonamido)piperidine-1,2-dicarboxylate

: 1471297-86-5
(2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

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

2: trifluoroacetic acid / dichloromethane / 20 °C

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

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

5: N-ethyl-N,N-diisopropylamine; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 17 h / 20 °C

6: 1,4-dioxane / 2 h / 45 - 50 °C

With lithium hydroxide monohydrate; water; ammonium chloride; benzotriazol-1-ol; mercaptoacetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;