HCID 131733446, compound → HCID 131733445, compound

Participants

Reaction Steps

Pyridinium chlorochromate (218 mg, 1.01 mmol) and molecular sieves were added to a solution of tert-butyl (3-(3-(((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl)sulfonyl)phenyl)-3-hydroxypropyl)carbamate (650 mg, 1.40 mmol) in CH2Cl2 (20 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered through a Celite, the filtrate was diluted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (60% EtOAc-hexanes gradient) gave tert-butyl (3-(3-(((1,1-dioxidotetrahydro-2H-thiopyran-4-yl)methyl)sulfonyl)phenyl)-3-oxopropyl)carbamate as a colorless liquid. Yield (0.438 g, 67%); 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1H), 8.28 (d, J=7.6 Hz, 1H), 8.16 (d, J=7.6 Hz, 1H), 7.83 (t, J=8.0 Hz, 1H), 6.87 (s, 1H), 3.51 (d, J=6.4 Hz, 2H), 3.32-3.28 (m, 4H), 3.28-3.23 (m, 2H), 3.20-3.13 (m, 1H), 3.04-3.01 (m, 1H), 2.32 (bs, 1H), 2.17-2.14 (m, 2H), 1.85-1.76 (m, 2H), 1.35 (s, 9H); MS: m/z 460.23 [M+H]+.

Provenance & Evidence