Reacción #1069771

Ecuación de reacción

sodium bicarbonate

Dimethylsulfide

Compound 1b

N-[(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl]-3-hydroxy-4-methoxypyridine-2-carboxamide

Benzoyl peroxide

→

title compound

N-{(3S,7R,8R,9S)-7-benzyl-9-methyl-8-[(methylthio)methoxy]-2,6-dioxo-1,5-dioxonan-3-yl}-3-hydroxy-4-methoxypyridine-2-carboxamide

Disolventes

ethyl acetate

diethyl ether

acetic acid

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic phase was separated
2. 2
   Lavadorinsed with water, brine (×2)
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otroto give a gum
5. 5
   Otroafforded 1.56 g (70%) of an off a white crystalline solid

Procedimiento

Compound 1b (2.0 g, 4.5 mmol) was dissolved in acetonitrile. Dimethylsulfide (6.6 mL) and acetic acid (2 mL) were added and the resulting mixture cooled to 0-5° C. (ice bath) under nitrogen. Benzoyl peroxide (6.36 g, 26 mmol) was added in several portions over 5 hours, then stirred for an additional 10 minutes, and then the reaction mixture was poured into a mixture of ethyl acetate and saturated aq. sodium bicarbonate (100 mL each). The organic phase was separated, rinsed with water, brine (×2), and concentrated in vacuo to give a gum. This gum upon addition of 50 mL of diethyl ether afforded 1.56 g (70%) of an off a white crystalline solid. m.p.=159-160° C. Spectral data were consistent with the title compound.

Fuente