[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:24]2[NH:25][CH2:26][C:27]([O:35]S(C)(=O)=O)=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:29]=2)[CH2:17][CH2:16][CH:15]([CH2:18]OS(C)(=O)=O)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:41].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]12[CH2:13][CH2:14][CH:15]([CH2:16][CH2:17]1)[CH2:18][N:25]1[C:26](=[O:41])[C:27]([OH:35])=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[N:29]=[C:24]21)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1A mixture of ethyl 2-(1-(benzyloxycarbonylamino)-4-((methylsulfonyloxy)methyl)cyclohexyl)-5-(methylsulfonyloxy)-1,6-dihydropyrimidine-4-carboxylate (2.25 g, 3.74 mmol) and cesium carbonate (1.22 g, 3.74 mmol) in DMF (40 mL) was heated at 60° C. for 18 h. The reaction mixture was then cooled and concentrated in vacuo. The residue was taken up in ethyl acetate (200 mL) and extracted with 0.2 M aq. NaOH (3×50 mL). The combined aqueous phase was washed with ethyl acetate (250 mL). The aqueous layer was then acidified with conc. HCl and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 extracts were dried (Na2SO4), filtered and concentrated to afford the title compound as a brown solid (400 mg). 1H NMR (500 MHz, CDCl3) δ: 10.81 (s, 1H), 7.29-7.36 (m, 6H), 5.29 (s, 1H), 5.10 (s, 2H), 4.41 (q, 2H, J=7.27 Hz), 4.13 (d, 2H, J=3.66 Hz), 2.43-2.47 (m, 2H), 1.94-2.02 9 m, 2H), 1.79-1.85 (m, 2H), 1.65-1.72 (m, 2H), 1.40 (t, 3H, J=7.17). LCMS (M+H)=428.26.
読み込み中…