Реакция #83113

ord-d3a3b1eeebe04963a7447f94ecf0b7fc

Уравнение реакции

CC(O)C1C(=O)N2C(C(=O)[O-])=C(SC3COC(COC(N)=O)C3)C(C)C12.[Na+]
product
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
CC(C)(C)C(=O)OCCl
chloromethyl pivalate
O=C([O-])O.[Na+]
sodium bicarbonate
[I-].[Na+]
sodium iodide
→
CC(O)C1C(=O)N2C(C(=O)OCOC(=O)C(C)(C)C)=C(SC3COC(COC(N)=O)C3)C(C)C12
desired product
CC(O)C1C(=O)N2C(C(=O)OCOC(=O)C(C)(C)C)=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 (2,2-Dimethyl-1-oxopropoxy)methyl Ester

Реактанты

CC(O)C1C(=O)N2C(C(=O)[O-])=C(SC3COC(COC(N)=O)C3)C(C)C12.[Na+]
product
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
CC(C)(C)C(=O)OCCl
chloromethyl pivalate
O=C([O-])O.[Na+]
sodium bicarbonate
[I-].[Na+]
sodium iodide

Реагенты

Нет

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

The title compound is prepared by the procedure of Example 407 using 0.460 g of product from Example 21, 0.24 ml of chloromethyl pivalate, 0.189 g of sodium bicarbonate and 0.252 g of sodium iodide to give after chromatography 0.32 g of the desired product.

Источник

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