Réaction #215683

Équation de réaction

Allyl 6β-[(1,3-dithiolan-2-ylidene)(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate

sodium 2-ethylhexanoate ethyl acetate

triphenylphosphine

→

title compound

Rendement 84.0%

Sodium 6β-[(1,3-dithiolan-2-ylidene)(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate

Rendement 84.0%

Conditions de réaction

Traitement

1. 1
   FiltrationThe resulting precipitate was collected by filtration
2. 2
   Lavagewashed with ethyl acetate and diethyl ether
3. 3
   Autredried in vacuo

Mode opératoire

Allyl 6β-[(1,3-dithiolan-2-ylidene)(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (459 mg, 1 mmol) was dissolved in 0.25N sodium 2-ethylhexanoate/ethyl acetate solution (4 mL), and treated with triphenylphosphine (30 mg) and tetrakis(triphenylphosphine)palladium(0) (30 mg). The reaction mixture was stirred at room temperature for 2 h under a nitrogen atmosphere. The resulting precipitate was collected by filtration, washed with ethyl acetate and diethyl ether, and dried in vacuo to yield the title compound (368 mg, 84%) as a light yellow powder: 1H NMR (D2O) δ 1.40 and 1.50 (each 3H, s, C2 -(CH3)2), 3.25-3.45 (4H, m, SCH2CH2S), 3.69 (3H, s, OCH3), 4.13 (1H, s, C3 -H), 5.45-5.52 (2H, m, C5 -H and C6).

Source