tert-Butyl {2-[3-(2,3-dihydro-1-ethyloxycarbonyl-3-oxo-indazol-2-yl)-propylsulfanyl]-benzoimidazol-1-yl}-acetate → {2-[3-(2,3-Dihydro-1-ethyloxycarbonyl-3-oxo-indazol-2-yl)-propylsulfanyl]-benzoimidazol-1-yl}-acetic acid
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[CH2:16][CH2:17][CH2:18][S:19][C:20]1[N:24]([CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[C:23]2[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=2[N:21]=1)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O.ClCCl>[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[N:7]1[CH2:16][CH2:17][CH2:18][S:19][C:20]1[N:24]([CH2:25][C:26]([OH:28])=[O:27])[C:23]2[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=2[N:21]=1)=[O:5])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
tert-Butyl {2-[3-(2,3-dihydro-1-ethyloxycarbonyl-3-oxo-indazol-2-yl)-propylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor G-01b, 63.8 mg, 0.1 mmol) is stirred in TFA/dichloromethane (1:1, 2 ml) at rt overnight. The solvents are removed in vacuo. The crude is taken up in chloroform (1 ml) and filtered over cotton wool. The solvent is removed in vacuuo and the residue is dried under high vacuum. This yields the title compound (6 mg) in 11% as a colourless oil: tR=2.24 min (LC-2), ESI-MS (pos.): m/z 455.11 [M+H]+, ESI-MS (neg.): m/z 453.22 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 1.31 (t, 3H, CH3), 2.03 (quint., 2H, CH2CH2N), 3.18 (m, 2H, SCH2), 4.23 (t, 2H, CH2N), 4.36 (q, 2H, OCH2), 4.94 (s, 2H, CH2CO2), 7.10-7.15 (m, 2H, m), 7.39 (t, 1 Harom), 7.46 (m, 2Harom), 7.70-7.78 (m, 2Harom), 7.87 (d, 1Harom)