Réaction #215685

Équation de réaction

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

HCl

→

title compound

6β-[(1,3-Dithiolan-2-ylidene)(ethoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylic acid

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   Autreat 0° C
2. 2
   ExtractionThe mixture was extracted with dichloromethane several times
3. 3
   LavageThe combined organic layer was washed with H2O and saturated NaCl solution
4. 4
   Séchagedried over Na2SO4
5. 5
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a solution of sodium 6β-[(1,3-dithiolan-2-ylidene)(ethoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (46 mg, 0.1 mmol) in 1 mL of H2O was added one drop (38 mg) of cone. HCl solution at 0° C. The mixture was extracted with dichloromethane several times. The combined organic layer was washed with H2O and saturated NaCl solution, dried over Na2SO4, and concentrated under reduced pressure to give the title compound (32 g, 74% yield) as a yellow oil: 1H NMR (D2O) δ 1.40 (3H, t, J=7Hz, CH2CH3), 1.55 and 1.66 (each 3H, s, C2 -(CH3)2), 3.33 (4H, s, SCH2CH2S), 4.31-4.41 (3H, m, C3 -H and OCH2CH3), 5.57 (1H, d, J=4Hz, C5-H), 5.82 (1H, dd, J=4 and 9Hz, C6-H), 9.03 (1H, d, J=9Hz, NH).

Source