Реакция #83044

ord-3976d0f5ed1c4d73ad5ec7a90b90cb72

Уравнение реакции

CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COC(N)=O)C3)C(C)C12
product
CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COC(N)=O)C3)C(C)C12
3-[[5-[[(Aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
O=C([O-])O.[Na+]
sodium bicarbonate
O
water
→
CC(O)C1C(=O)N2C(C(=O)[O-])=C(SC3COC(COC(N)=O)C3)C(C)C12.[Na+]
desired product
Выход 55.7%
CC(O)C1C(=O)N2C(C(=O)[O-])=C(SC3COC(COC(N)=O)C3)C(C)C12.[Na+]
3-[[5-[[(Aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt
Выход 55.7%

Реактанты

CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COC(N)=O)C3)C(C)C12
product
CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COC(N)=O)C3)C(C)C12
3-[[5-[[(Aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]thio]-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
O=C([O-])O.[Na+]
sodium bicarbonate
O
water

Реагенты

[Pd]
palladium/carbon

Растворители

C1COCCO1
dioxane

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

The title compound is prepared by the procedure of Example 18 using 0.126 g of product from Example 20, 0.0223 g of sodium bicarbonate, 1.4 ml of water, 7.8 ml of dioxane, and 0.070 g of 10% palladium/carbon to give 0.055 g of the desired product as a yellow solid.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05623081uspto-grants-1997_04