HCID 21059932, compound → HCID 86595785, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 5-{[tert-butyl(diphenyl)silyl]oxy}pentanethioamide (4.97 g, 13.37 mmol) in 1,4-dioxane (50 mL). Add magnesium carbonate hydroxide pentahydrate (3.25 g, 0.5 mmol) and (3S)-ethyl 3-(1,3-benzodioxol-5-yl)-6-chloro-5-oxohexanoate (see Scheme 2, Example M) (4.18 g, 13.37 mmol). Heat to 60° C. for 5 hrs. Upon cooling, the reaction was filtered through a pad of celite and concentrated in vacuo, and purified via silica gel chromatography (eluent: 9:1 Hexane:Ethyl Acetate) to give the product as a yellow oil. Yield: 6.55 g (78%) 1H NMR (DMSO-d6) δ7.64–7.58 (m, 4H), 7.48–7.39 (m, 6H), 6.95–6.93 (m, 1H), 6.85–6.82 (m, 1H), 6.73–6.69 (m, 1H), 5.92 (s, 2H), 3.93–3.85 (q, 2H), 3.70–3.64 (t, 2H), 3.46–3.38 (m, 1H), 3.00–2.85 (m, 4H), 2.68–2.53 (m, 2H), 1.83–1.74 (m, 2H), 1.62–1.53 (m, 2H), 1.08–0.99 (t, 3H), 0.99 (s, 9H).

Provenance & Evidence