Reacción #4211

Ecuación de reacción

Trifluoroacetic acid

(2S-trans)-[1-[[2-(3,4-dihydroxyphenyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, 1,1-dimethylethyl ester

monopotassium

anisole

→

title compound

(2S-trans)-(3-Amino-2-methyl-4-oxo-1-azetidinyl)phosphonic acid, 2-(3,4-dihydroxyphenyl)-2-oxoethyl ester, trifluoroacetate salt

Disolventes

dichloromethane

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvents removed in vacuo at room temperature
2. 2
   Otroyielding a yellow oily residue
3. 3
   OtroThe residue was triturated with hexanes (2×10 ml)
4. 4
   OtroThe solid was dried in vacuo

Procedimiento

To a suspension of (2S-trans)-[1-[[2-(3,4-dihydroxyphenyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, 1,1-dimethylethyl ester, monopotassium salt (117 mg, 0.25 mmol) in 2.5 ml of dry dichloromethane was added 100 μl of anisole and the mixture was then cooled to 0° C. in an ice bath under argon. Trifluoroacetic acid (1 ml) was added and the mixture stirred for two hours. The reaction mixture was diluted with 5 ml of dry toluene and the solvents removed in vacuo at room temperature yielding a yellow oily residue. The residue was triturated with hexanes (2×10 ml) followed by trituration with ether (2×10 ml). The solid was dried in vacuo yielding the title compound.

Fuente