Technology Process of (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-16-nitro-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene
There total 13 articles about (9S,12S)-12-[N-(benzyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-16-nitro-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-16-nitro-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene;
With
trifluoroacetic acid;
at 20 ℃;
for 0.333333h;
N-(Benzyloxycarbonyloxy)succinimide;
With
triethylamine;
In
tetrahydrofuran;
at 20 ℃;
for 1h;
DOI:10.1021/jo990432w
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: triethylamine / tetrahydrofuran / 1 h / -78 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 84 percent / tetrahydrofuran; hexane / -78 - 20 °C
3.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
3.2: 83 percent / trisyl azide / tetrahydrofuran; toluene / 0.03 h / -78 °C
4.1: MeMgBr / diethyl ether / 0.03 h / 0 °C
4.2: 96 percent / diethyl ether / 0.17 h / 0 °C
5.1: 99 percent / hydrogen / Pd/C / methanol / 1 h
6.1: 90 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 1.33 h / 20 °C
7.1: BCl3 / CH2Cl2 / -78 - 0 °C
7.2: 99 percent / Boc2O; triethylamine / tetrahydrofuran / 2 h / 20 °C
8.1: potassium carbonate; molecular sieves 3A / dimethylsulfoxide / 2 h / 20 °C
9.1: trifluoroacetic acid / 0.33 h / 20 °C
9.2: 95 percent / triethylamine / tetrahydrofuran / 1 h / 20 °C
With
n-butyllithium; 3 A molecular sieve; methylmagnesium bromide; hydrogen; boron trichloride; potassium hexamethylsilazane; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; toluene;
1.1: Acylation / 2.1: Metallation / 2.2: Substitution / 3.1: Metallation / 3.2: Substitution / 4.1: Substitution / 4.2: Substitution / 5.1: Hydrogenolysis / 6.1: coupling / 7.1: Hydrolysis / 7.2: Acylation / 8.1: Cyclization / 9.1: Hydrolysis / 9.2: Acylation;
DOI:10.1021/jo990432w
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 99 percent / hydrogen / Pd/C / methanol / 1 h
2.1: 90 percent / 1-hydroxybenzotriazole hydrate; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH2Cl2 / 1.33 h / 20 °C
3.1: BCl3 / CH2Cl2 / -78 - 0 °C
3.2: 99 percent / Boc2O; triethylamine / tetrahydrofuran / 2 h / 20 °C
4.1: potassium carbonate; molecular sieves 3A / dimethylsulfoxide / 2 h / 20 °C
5.1: trifluoroacetic acid / 0.33 h / 20 °C
5.2: 95 percent / triethylamine / tetrahydrofuran / 1 h / 20 °C
With
3 A molecular sieve; hydrogen; boron trichloride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; dichloromethane; dimethyl sulfoxide;
1.1: Hydrogenolysis / 2.1: coupling / 3.1: Hydrolysis / 3.2: Acylation / 4.1: Cyclization / 5.1: Hydrolysis / 5.2: Acylation;
DOI:10.1021/jo990432w
