Technology Process of 3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-3S-hydroxy-2R-methyl-N,N-diethylpropionamide
There total 8 articles about 3-(5S-isopropyl-4S-methoxycarbonyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-3S-hydroxy-2R-methyl-N,N-diethylpropionamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
(4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester;
With
lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane;
at -78.8 ℃;
for 0.75h;
With
dimethylaluminum chloride;
In
tetrahydrofuran; hexane;
at -78.8 ℃;
for 1h;
N,N-diethyl-2R-methyl-3-oxopropionamide;
In
tetrahydrofuran; hexane;
at -85 - -20 ℃;
DOI:10.1021/ja991175f
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 60 percent / K2OsO2(OH)4; hydroquinine 1,4-phthalazinediyl diether; aq. N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 49 h / 20 °C
2.1: BF3*OEt2 / CH2Cl2 / 1.83 h / 20 °C
3.1: acetyl bromide / CH2Cl2 / 2.5 h / 20 °C
4.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C
5.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C
5.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating
6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C
6.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C
6.3: tetrahydrofuran; hexane / -85 - -20 °C
With
hydrogenchloride; palladium dihydroxide; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); Acetyl bromide; boron trifluoride diethyl etherate; hydrogen; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol;
1.1: dihydroxylation / 2.1: Condensation / 3.1: Ring cleavage / 4.1: azidation / 5.1: Hydrogenation / 5.2: Cyclization / 6.1: Metallation / 6.2: Substitution / 6.3: Condensation;
DOI:10.1021/ja991175f
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: BF3*OEt2 / CH2Cl2 / 1.83 h / 20 °C
2.1: acetyl bromide / CH2Cl2 / 2.5 h / 20 °C
3.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C
4.1: H2; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C
4.2: 89 percent / p-TsOH*H2O / toluene / 2.75 h / Heating
5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.75 h / -78.8 °C
5.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 1 h / -78.8 °C
5.3: tetrahydrofuran; hexane / -85 - -20 °C
With
hydrogenchloride; palladium dihydroxide; sodium azide; Acetyl bromide; boron trifluoride diethyl etherate; hydrogen; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide;
1.1: Condensation / 2.1: Ring cleavage / 3.1: azidation / 4.1: Hydrogenation / 4.2: Cyclization / 5.1: Metallation / 5.2: Substitution / 5.3: Condensation;
DOI:10.1021/ja991175f
