Potassium → HCID 11142198, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(R)acetoxy-3(R)-[1(R)t-butyldimethylsilyloxyethyl]azetidin-2-one (2.87 g) in dioxane (40 ml) the potassium salt of methoxythioacetic acid (1.7 g) was added. Zinc bromide (2.7 g) was added to the resulting suspension and the reaction mixture was stirred for 4 hours at 40° C. The reaction mixture was then cooled at room temperature and poured in a mixture of ethyl acetate and water. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography to give 2.99 g of the title product (90% yield). NMR (CDCl3) δ (ppm): 0.1 (6H, s); 0.83 (9H, s); 1.16 (3H, d); 3.13 (1H, dd); 3.42 (3H, s), 4.01 (2H, s) 4.20 (1H, m); 5.22 (1H, d); 6.55 (1H, s)

Provenance & Evidence