HCID 86602077, 화합물 → HCID 58746705, 화합물
반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([NH:26][C:27](=[O:44])[C@@H:28]([NH:36]C(=O)OC(C)(C)C)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH:19]=2)=[CH:14][CH:13]=1>FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:36][C@@H:28]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:27]([NH:26][C@H:10]([C:2]1[NH:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH:19]=2)=[CH:14][CH:13]=1)=[O:44]참가 물질
4
실험 절차
Tert-butyl [(1S)-2-({1-(1H-benzimidazol-2-yl)-2-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl}amino)-1-benzyl-2-oxoethyl]carbamate (10 mg, 0.016 mmol) was dissolved in a mixture of trifluoroacetic acid (1 mL) and methylene chloride (1 mL) and stirred for 45 minutes. The solvent was removed in vacuo. The diastereomers alpha to the benzimidazole were resolved through preparative LCMS purification to yield 5.5 mg (95%) of (2S)-2-amino-N-{(1R)-1-(1H-benzimidazol-2-yl)-2-[4-({1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl}-3-phenylpropanamide (Peak A) and 5.5 mg (95%) of (2S)-2-amino-N-{(1S)-1-(1H-benzimidazol-2-yl)-2-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]ethyl}-3-phenylpropanamide (Peak B). Peak A: 1H NMR (500 MHz, CD3OD): δ 7.84 (d, J=8.4 Hz, 2H), 7.76–7.79 (m, 2H), 7.56–7.59 (m, 2H), 7.43 (d, J=8.4 Hz, 2H), 7.28–7.31 (m, 3H), 7.10–7.13 (m, 2H), 6.93 (s, 1H), 5.59–5.63 (m, 1H), 4.19–4.22 (m, 1H), 3.50–3.55 (m, 1H), 3.32–3.41 (m, 1H), 3.08–3.13 (m, 1H), 2.86–2.91 (m, 1H); LCMS found for C27H25N5O4S (M+H)+: m/z=516.0 Peak B: 1H NMR (500 MHz, CD3OD): δ 7.77–7.82 (m, 4H), 7.62–7.64 (m, 2H), 7.41 (d, J=8.4 Hz, 2H), 6.88–7.01 (m, 6H), 5.61–5.65 (m, 1H), 4.14–4.18 (m, 1H), 3.48–3.53 (m, 2H), 2.97–3.25 (m, 2H); LCMS found for C27H26N5O4S (M+H)+: m/z=516.0