Carbon Disulfide → HCID 15297251, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of allyl 6β-[(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (713 mg, 2 mmol) in 2 mL of sieve-dried dimethylformamide at 0° C. was added carbon disulfide (1 mL), then sodium hydride, 60% (160 mg, 4 mmol), portionwise. The reaction mixture was stirred at 0° C. for 10 min under a nitrogen atmosphere, and treated with dibromoethane (413 mg, 2.2 mmol). The mixture was stirred at 0° C. for 30 min, diluted with toluene, washed with water and saturated NaCl solution, and dried over Na2SO4. The solution was concentrated to give a brown oil, which was chromatographed on silica gel eluting with chloroform-ethyl acetate (95:5) to yield the title compound (811 mg, 88%) as a yellow foam: IR (CHCl3) 1790, 1750, 1685 cm-1; 1 H NMR (CDCl3) δ 1.50 and 1.67 (each 3H, s, C2-(CH 3)2), 3.33 (4H, s, SCH2CH2S), 3.88 (3H, s, CO2CH3), 4.48 (1H, s, C3 -H), 4.64-4.68 (2H, m, OCH2CH=CH2), 5.25-5.42 (2H, m, OCH2CH=CH2), 5.58 (1H, d, J=4Hz, C5 -H), 5.83 (1H, dd, J=4 and 9Hz, C6 -H), 5.85-6.00 (1H, m, OCH2CH=CH2), 8.97 (1H, d, J=9Hz, NH).

Provenance & Evidence