HCID 71278246, compound → HCID 71268741, compound

Participants

Reaction Steps

tert-Butyl[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(fluoromethyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]carbamate (C25) was converted to the product according to the general procedure for the synthesis of (4aR,6R,8aS)-8a-(2-fluorophenyl)-6-[(propan-2-yloxy)methyl]-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine, trifluoroacetate salt (2) in Example 2. In this case, the reversed-phase HPLC purification was carried out using a different system (Column: Waters XBridge C18, 5 μm; Mobile phase A: 0.03% ammonium hydroxide in water (v/v); Mobile phase B: 0.03% ammonium hydroxide in acetonitrile (v/v); Gradient: 5% to 100% B), affording the product as an oil. Yield: 17 mg, 0.054 mmol, quantitative. LCMS m/z 317.2 (M+1). 1H NMR (600 MHz, DMSO-d6) δ 1.56-1.64 (m, 1H), 1.66-1.72 (m, 1H), 2.88 (dd, J=13.2, 3.5 Hz, 1H), 3.02 (br d, J=13 Hz, 1H), 3.14-3.21 (m, 1H), 3.88 (d, half of AB quartet, J=12.3 Hz, 1H), 3.92-4.01 (m, 2H), 4.38-4.57 (m, 2H), 7.21-7.26 (m, 1H), 7.28-7.34 (m, 1H), 7.36-7.41 (m, 1H).

Provenance & Evidence