تفاعل #1069771

معادلة التفاعل

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

المذيبات

ethyl acetate

diethyl ether

acetic acid

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe organic phase was separated
2. 2
   غسيلrinsed with water, brine (×2)
3. 3
   تركيزconcentrated in vacuo
4. 4
   أخرىto give a gum
5. 5
   أخرىafforded 1.56 g (70%) of an off a white crystalline solid

الإجراء التجريبي

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.

المصدر