benzyl (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(methylthio)ethylcarbamate → HCID 58287045, compound

Participants

Reaction Steps

A stirred solution of the product from Example 27.3 (2.007 g, 6.17 mmol) in isopropanol (34 ml) and 2M potassium hydroxide (15 ml) was heated at 80° C. for 64 h. The reaction mixture was concentrated to remove isopropanol. The residue was diluted with water and extracted with diethyl ether (3×), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (ethyl acetate-petrol, 2:1 then methanol-ethyl acetate, 2:98) giving a pale yellow oil (0.913 g, 77%). 1H NMR (CDCl3) δ 4.06 (m, 2H), 3.79 (m, 1H), 2.90 (m, 1H), 2.61 (dd, J=13.2, 4.5 Hz, 1H), 2.44 (dd, J=13.2, 8.7 Hz, 1H), 2.12 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H). 13C NMR (CDCl3) δ 109.5, 79.0, 66.9, 52.7, 39.9, 26.9, 25.6, 16.3, 14.6.

Provenance & Evidence