N#N.[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[O:17][C:18]([CH2:21][OH:22])=[CH:19][CH:20]=2)[CH:14]=1>C(C#N)(C)=O.O=[Mn]=O>[Cl:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[CH2:6][O:7][C:8](=[O:23])[NH:9][C:10]1[CH:11]=[N:12][N:13]([CH2:15][C:16]2[O:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=2)[CH:14]=1In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [1-(5-hydroxymethyl-furan-2-ylmethyl)-1H-pyrazol-4-yl]-carbamic acid 2-chloro-benzyl ester (300 mg, 0.83 mmol) in AcCN (8.0 mL) was treated at rt with MnO2 (400 mg, 4.15 mmol). The reaction mixture was stirred at rt overnight before being filtered through Celite and the solvent was removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=0.90 min; [M+H]+=360.28. 1H NMR (400 MHz, CDCl3) δ 5.32 (s, 5H), 6.47 (s, 1H), 6.64 (s, 1H), 7.20 (s, 1H), 7.30 (s, 1H), 7.37-7.45 (m, 1H), 7.45 (s, 2H), 7.79 (s, 1H), 9.63 (s, 1H).
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