Technology Process of tert-butyl {(1R,2S)-1-[(16S,19R)-15,18-dioxo-16-(propan-2-yl)-2,5,8,11-tetraoxa-14,17,20-triazabicyclo[20.2.2]hexacosa-1(24),22,25-trien-19-yl]-1-hydroxy-3-phenylpropan-2-yl}carbamate
There total 9 articles about tert-butyl {(1R,2S)-1-[(16S,19R)-15,18-dioxo-16-(propan-2-yl)-2,5,8,11-tetraoxa-14,17,20-triazabicyclo[20.2.2]hexacosa-1(24),22,25-trien-19-yl]-1-hydroxy-3-phenylpropan-2-yl}carbamate which
guide to synthetic route it.
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synthetic route:
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180968-37-0
[(1S,2R)-1-Benzyl-2-hydroxy-2-((16S,19R)-16-isopropyl-15,18-dioxo-2,5,8,11-tetraoxa-14,17,20-triaza-bicyclo[20.2.2]hexacosa-1(25),22(26),23-trien-19-yl)-ethyl]-carbamic acid tert-butyl ester
- Guidance literature:
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Multi-step reaction with 8 steps
1: 1-hydroxybenzotriazole, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature
2: pyridine / CH2Cl2 / 12 h / 0 - 20 °C
3: K2CO3, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C
4: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C
5: formic acid, H2 / 10percent Pd/C / methanol / 3 h / 760 Torr
6: ethanol / 24 h / 80 °C
7: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature
8: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature
With
pyridine; lithium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm950641i
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180968-37-0
[(1S,2R)-1-Benzyl-2-hydroxy-2-((16S,19R)-16-isopropyl-15,18-dioxo-2,5,8,11-tetraoxa-14,17,20-triaza-bicyclo[20.2.2]hexacosa-1(25),22(26),23-trien-19-yl)-ethyl]-carbamic acid tert-butyl ester
- Guidance literature:
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Multi-step reaction with 8 steps
1: 1-hydroxybenzotriazole, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature
2: pyridine / CH2Cl2 / 12 h / 0 - 20 °C
3: K2CO3, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C
4: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C
5: formic acid, H2 / 10percent Pd/C / methanol / 3 h / 760 Torr
6: ethanol / 24 h / 80 °C
7: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature
8: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature
With
pyridine; lithium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm950641i
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180968-37-0
[(1S,2R)-1-Benzyl-2-hydroxy-2-((16S,19R)-16-isopropyl-15,18-dioxo-2,5,8,11-tetraoxa-14,17,20-triaza-bicyclo[20.2.2]hexacosa-1(25),22(26),23-trien-19-yl)-ethyl]-carbamic acid tert-butyl ester
- Guidance literature:
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Multi-step reaction with 7 steps
1: pyridine / CH2Cl2 / 12 h / 0 - 20 °C
2: K2CO3, tetrabutylammonium iodide / dimethylsulfoxide / 4 h / 70 °C
3: hydroxyammonium chloride, aq. AcONa / ethanol / 1.5 h / 60 °C
4: formic acid, H2 / 10percent Pd/C / methanol / 3 h / 760 Torr
5: ethanol / 24 h / 80 °C
6: 0.4 M aq. LiOH / dioxane / 16 h / Ambient temperature
7: 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide hydrochloride / tetrahydrofuran / 120 h / Ambient temperature
With
pyridine; lithium hydroxide; formic acid; hydroxylamine hydrochloride; hydrogen; sodium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jm950641i