反应详情

The title compound was prepared as described in General Method 9 using 3.0 g (10.86 mmol) of (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (prepared in Example WWWW), 3.98 g (11.40 mmol) of toluene-4-thiosulfonic acid S-(4-amino-2-tert-butyl-5-methyl-phenyl) ester (prepared in Example HHHH), 4.50 g of anhydrous K2CO3 and 54 mL DMF. The reaction was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated. The crude material was purified by flash silica gel chromatography, eluting with EtOAc, to give the title compound, m.p. 147°-149° C. (dec.). 1H-NMR (DMSO-d6) δ 0.89 (d, 3 H), 0.93 (d, 3 H), 1.42 (s, 9 H), 1.71 (s. 3 H), 1.85-1.93 (m, 2 H), 2.15 (m, 1 H), 2.41-2.50 (m, 2 H, partially obscured by DMSO), 2.67 (d of ABX q, 1 H), 2.89 (d of ABX q, 1 H), 6.55 (s, 1 H), 6.60 (s, 1 H), 6.64 (d, 2H), 6.93 (d, 2H), 9.13 (br s, 1 H).

1. customThe title compound was prepared
2. customThe reaction was quenched with saturated NH4Cl solution
3. extractionextracted with EtOAc
4. dry with materialThe organic phase was dried over MgSO4
5. concentrationconcentrated
6. customThe crude material was purified by flash silica gel chromatography
7. washeluting with EtOAc