p-Toluenesulfonic acid monohydrate → 3-methoxy-2-methoxymethyl-2-methyl-N-(3-oxo-propyl)-propionamide
Reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][NH:7][C:8](=[O:17])[C:9]([CH2:14][O:15][CH3:16])([CH3:13])[CH2:10][O:11][CH3:12])C.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(C)=O>[CH3:16][O:15][CH2:14][C:9]([CH2:10][O:11][CH3:12])([CH3:13])[C:8]([NH:7][CH2:6][CH2:5][CH:4]=[O:3])=[O:17]Participants
4
Procedure
To a solution of 3 g of N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide in 71 mL of acetone was added 3.91 g of TsOH.H2O. The mixture was stirred over night at rt, quenched with sat.-NaHCO3 and extracted with DCM. The organic phase was washed with brine, dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc from 100/0 to 0/100 as eluant to yield 2.19 g of 3-methoxy-2-methoxymethyl-2-methyl-N-(3-oxo-propyl)-propionamide