Dichloromethane → 2-amino-3-{4-[4-(2-hydroxycarbamoylethyl)-phenoxy]-phenyl}-N,N-dimethylpropionamide hydrochloride
Reaction equation
C(OC(=O)[NH:7][CH:8]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](=[O:28])[NH:26][OH:27])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(Cl)[Cl:36]>>[ClH:36].[NH2:7][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25](=[O:28])[NH:26][OH:27])=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)[C:29]([N:30]([CH3:31])[CH3:32])=[O:33]Participants
3
Conditions
- Temperature
- 2.5 °C
Procedure
The hydroxamate 8 (3.4 g) was dissolved in CH2Cl2 and cooled to 0-5° C. Hydrogen chloride gas was bubbled through this solution for 20 min. The bubbling was discontinued and the reaction mixture was stirred at room temperature for 1 h. The excess HCl was degassed and the CH2Cl2 was removed. The residual solid was triturated with EtOAc (2×50 mL), decanted, and dried to yield the desired compound 9 as a white amorphous solid (2.9 g, 98%). 1H NMR (DMSO-d6): 10.39 (s, 1H), 7.21 (d, J=8.4 Hz, 4H), 6.95 (d, J=8.4 Hz, 2H), 6.99 (d, J=8.4 Hz, 2H), 4.55 (m, 1H), 2.95-2.99 (m, 2H), 2.82 (s, 3H), 2.80 (t, J=8.0 Hz, 2H), 2.73 (s, 3H), 2.25 (t, J=8.0 Hz, 2H); LCMS (m/e): Obsd. 372.0, Calcd. 371.43