Methanol → HCID 11353239, compound

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Reaction Steps

To a solution of 2-tert-Butoxy carbonylamino-3-[4-(4,6-diphenylpyrimidin-2-yl)-benzylsulfanyl]-propionic acid methyl ester, 0.18 g (0.32 mmol) in 10 mL of tetrahydrofuran and 5 mL of methanol was added 1.62 mL of 1.0M aq. KOH. The solution was stirred for 1 h at room temperature. The solution was diluted with 10 mL of water and acidified to pH 1-2. The aqueous was extracted with 3×30 mL portions of diethyl ether. The organic layers were combined, washed with sat. aq. NaHCO3, sat. aq. NaCl, dried (MgSO4). The solution was concentrated to the desired product in 0.10 g (57%) as an off-white solid. MP 250° C. decomp, Rf=0.09 (100% Ethyl Acetate); 1H NMR (DMSO-d6) 8.57 (d, 2H, J=9.3), 8.52-8.46b (m, 5H), 7.60-7.58 (m, 6H), 7.51 (d, 2H, J=9.3), 4.11 (m, 1H), 3.86 (s, 3H), 2.81 (dd, 1H, J=14.8, 5.0 Hz), 2.67 (dd, 1H, J=15.3, 10.3), 1.39 (s, 9H). LCMS m/z calcd for C31H31N3O4S: 541.2, found 542.6(M+1)

Provenance & Evidence