Water → 2-[2-(4-Aminophenyl)ethyl]-5-{[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl}-6-hydroxy-2-(propan-2-yl)-2,3-dihydro-4h-pyran-4-one

Participants

Reaction Steps

A solution of {4-[2-(4-hydroxy-2-isopropyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-ethyl]-phenyl}-carbamic acid 1,1-dimethylethyl ester (0.26 g, 0.69 mmol; prepared in Example QQQQQ) in CH2Cl2 was cooled to 5° C. and treated with a steady stream of gaseous HCI for 5 minutes. The solution was concentrated, and the residue was triturated with ether. The crude material was dissolved in DMF (5 mL) and treated with 1.0 g (7.0 mmol) of K2CO3 and 0.25 g (0.69 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxymethyl-5-methyl-phenyl) ester (prepared in Example FFF). The reaction mixture was stirred overnight at room temperature. Water (30 mL) and EtOAc (50 mL) were added; the mixture was cooled in an ice bath and acidified to pH 5.5 with AcOH. The organic layer was separated, washed with brine, dried (MgSO4), and concentrated. The product was chromatographed on silica gel, eluting with CHCl3 :MeOH (90:10) to give the title compound, m.p. 139-141° C. 1H NMR (DMSO-d6) δ 0.88 (m, 6 H), 1.42 (s, 9 H), 1.87 (m, 5 H), 2.14 (m, 1 H), 2.40 (m, partially obscured by DMSO, 2 H), 2.66 (d of ABXq, 1 H), 2.88 (d, of ABXq, 1 H), 4.30 (s, 2 H), 4.90 (br s, 1 H), 6.43 (d, 2 H), 6.64 (s, 1 H), 6.77 (d, 2 H), 7.20 (s, 1 H).

Provenance & Evidence