Potassium Carbonate → Dimethylsulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(3-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methylphenyl ester

Participants

Reaction Steps

The compound was synthesized following General Method 9 and using 77 mg (0.2 mmol) of 4-hydroxy-6,6-bis-[2-(3-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example XX), 100 mg (0.2 mmol) of toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example UUU), 18 mg (0.8 mmol) of K2CO3 and 5 mL of DMF. The reaction was worked up as described and chromatographed on silica gel, eluting with (1:1 CH2Cl2 :EtOAc+2% MeOH), to give the title compound. 1H NMR (DMSO-d6) δ 1.45 (s, 9 H), 1.9 (s, 3 H), 2.95 (m, 4 H), 2.6 (m, 4 H), 2.95 (s, 6 H), 3.35 (m, 2 H), 6.60 (m, 6 H), 6.8 (s, 1 H), 7.05 (t, 2 H), 7.15 (s, 1 H), 9.25 (s, 2 H).

Provenance & Evidence