Sodium Bicarbonate → HCID 11716529, Verbindung

Reaktionsgleichung

FC(F)(F)C(O)=O.[NH2:8][C@@H:9]([CH2:13][O:14][C:15]([O:17][C:18]1[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=1[CH:27]([CH3:29])[CH3:28])=[O:16])[C:10]([OH:12])=[O:11].C(=O)(O)[O-].[Na+]>O.CC#N>[NH2:8][C@@H:9]([CH2:13][O:14][C:15]([O:17][C:18]1[C:23]([CH:24]([CH3:25])[CH3:26])=[CH:22][CH:21]=[CH:20][C:19]=1[CH:27]([CH3:29])[CH3:28])=[O:16])[C:10]([OH:12])=[O:11]

Komponenten

Versuchsvorschrift

To a stirred solution of compound (8) in H2O and MeCN (20/1 v/v) was added a saturated aqueous sodium bicarbonate solution dropwise. The pH of this reaction mixture was monitored closely and the desired product precipitated as a white solid after the pH was adjusted to 7. The mixture was filtered and the title compound (3) was collected and dried in vacuo. 1H-NMR (400 MHz, CDCl3): δ 7.15-7.22 (m, 3H), 4.64-4.68 (dd, J=11.6, 3.2 Hz, 1H), 4.55-4.60 (dd, J=11.6, 6.8 Hz, 1H), 3.28-3.30 (dd, J=6.8, 3.2 Hz, 1H), 2.99-3.04 (m, 2H), 1.18-1.19 (d, J=6.4 Hz, 12H). MS (ESI) m/z 310.3 (M+H)+.