Réaction #83043

Équation de réaction

hydrogen

product

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

sodium bicarbonate

water

→

desired product

Rendement 67.0%

[[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

Rendement 67.0%

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture is filtered through a pad of diatomaceous earth
2. 2
   Lavagewashed with water
3. 3
   Concentrationconcentrated to 1/2 volume
4. 4
   ExtractionThe solution is extracted with ethyl acetate
5. 5
   Autrethe aqueous layer is freeze-dried
6. 6
   AutreThe product is purified

Mode opératoire

A mixture of 0.181 g of product from Example 17, 0.032 g of sodium bicarbonate, 2 ml of water, 11 ml of dioxane and 0.100 g of 10% palladium/carbon is reduced in a Parr apparatus at 42 psi of hydrogen for 3 hours. The reaction mixture is filtered through a pad of diatomaceous earth, washed with water and concentrated to 1/2 volume. The solution is extracted with ethyl acetate and the aqueous layer is freeze-dried. The product is purified using C18 reverse phase chromatography (95/5 water/ethyl alcohol) to give 0.095 g of the desired product as a yellow solid.

Source