Reaktionsgleichung
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:41]=[CH:40][C:16]([CH2:17][N:18]([CH2:27][C:28]3[CH:39]=[CH:38][C:31]([O:32][CH2:33][C:34]([O:36]C)=[O:35])=[CH:30][CH:29]=3)[S:19]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:41]=[CH:40][C:16]([CH2:17][N:18]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:38][CH:39]=3)[S:19]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)(=[O:20])=[O:21])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of methyl (4-{[{4-[(4-butylphenyl)ethynyl]benzyl}(2-thienylsulfonyl)amino]-methyl}phenoxy)acetate (30 mg, 0.051 mmol) in MeOH/THF (4 ml, (1/1)) was added an aqueous solution of NaOH (2 mL, 1N). The reaction mixture was stirred at rt for 2 hrs. Then an aqueous solution of HCl (9 mL, 1N) was added and extracted with Et2O (2×10 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure to give 30 mg (97%) of the title compound as a green oil. HPLC, Rt: 5.3 min (purity: 95.3%). LC/MS, M+(ESI): 574.2, M−(ESI): 572.3. 1H NMR (CDCl3) δ: 7.60 (m, 2H), 7.44 (d, J=8.3 Hz, 2H), 7.38 (d, J=7.9 Hz, 2H), 7.17 (d, J=7.9 Hz, 2H), 7.12 (m, 1H), 7.05 (m, 4H), 6.80 (d, J=8.7 Hz, 2H), 4.66 (s, 2H), 4.33 (s, 2H), 4.31 (s, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.61 (m, 2H), 1.37 (m, 2E), 0.94 (t, J=7.4 Hz, 3H).
Aufarbeitung
- extractionextracted with Et2O (2×10 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- customthe solvents were removed under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-7dadb954ea7940d4be801c2842f7ca75
- Quelldatensatz
- uspto-grants-2011_05
- Patentnummer
- US07947851B2
Verknüpfte Notizen
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