Reacción #83047

ord-29230e4547a24481bad81faf5ef3b3f2

Ecuación de reacción

CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COc4ccccc4)C3)C(C)C12
product
CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COc4ccccc4)C3)C(C)C12
6-(1Hydroxyethyl)-4-methyl-7-oxo-3-[[tetrahydro-5-(phenoxymethyl)-3-furanyl]thio]-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(COc4ccccc4)C3)C(C)C12.[Na+]
desired product
Rendimiento 20.4%
CC(O)C1C(=O)N2C(C(=O)[O-])=C(SC3COC(COc4ccccc4)C3)C(C)C12.[Na+]
6-(1-Hydroxyethyl)4-methyl-7-oxo-3-[[tetrahydro-5-(phenoxymethyl)-3-furanyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monosodium salt
Rendimiento 20.4%

Reactantes

CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COc4ccccc4)C3)C(C)C12
product
CC(O)C1C(=O)N2C(C(=O)OCc3ccc([N+](=O)[O-])cc3)=C(SC3COC(COc4ccccc4)C3)C(C)C12
6-(1Hydroxyethyl)-4-methyl-7-oxo-3-[[tetrahydro-5-(phenoxymethyl)-3-furanyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester
O=C([O-])O.[Na+]
sodium bicarbonate
O
water

Reactivos

[Pd]
palladium/carbon

Disolventes

C1COCCO1
dioxane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

The title compound is prepared by the procedure of Example 18 using 0.320 g of product from Example 25, 0.054 g of sodium bicarbonate, 3.5 ml of water, 8.3 ml of dioxane and 0.166 g of 10% palladium/carbon to give 0.052 g of the desired product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05623081uspto-grants-1997_04