Hydrochloric Acid → HCID 86675874, compound

Participants

Reaction Steps

To a solution of (2R,3R)-1-((1R,5S)-10,10-dimethyl-3,3-dioxo-3lambda*6*-thia-4-aza-tricyclo[5.2.1.0*1,5*]dec-4-yl)-3-ethoxy-2-methyl-hept-6-en-1-one (245 mg, 0.64 mmol) in tetrahydrofuran (12 mL) was added a lithium hydroxide solution (2 M aqueous, 5 mL). The mixture was heated to reflux for 16 hours then cooled to room temperature and acidified to pH 1 with 2 M hydrochloric acid (15 mL). The aqueous layer was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, filtered and evaporated to give a colourless gum, which was purified by silica gel chromatography using iso-hexanes/ether 1:1 to give the title compound (78 mg, 65%) as a colourless gum. 1H NMR (300 MHz, CDCl3) δ 1.17 (d, J=7.1 Hz, 3H), 1.20 (t, J=7.5 Hz, 3H), 1.55-1.65 (m, 2H), 2.05-2.30 (m, 2H), 2.72-2.83 (m, 1H), 3.52-3.62 (m, 3H), 4.95-5.10 (m, 2H), 5.75-5.90 (m, 1H).

Provenance & Evidence