Technology Process of (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one
There total 12 articles about (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid;
With
benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 0.5h;
1-hydroxyguanidine;
In
N,N-dimethyl-formamide;
at 100 ℃;
for 2h;
Microwave irradiation;
- 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: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C
9.2: 2 h / 100 °C / Microwave irradiation
With
dirhodium tetraacetate; sodium tetrahydroborate; n-butyllithium; lithium hydroxide monohydrate; ethanol; water; 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; dichloromethane; N,N-dimethyl-formamide;
- Guidance literature:
-
Multi-step reaction with 2 steps
1.1: lithium hydroxide; water / tetrahydrofuran / 20 °C
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C
2.2: 2 h / 100 °C / Microwave irradiation
With
water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide;
In
tetrahydrofuran; N,N-dimethyl-formamide;