p-Toluenesulfonic acid monohydrate → 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide Ditosylate
Reaction equation
[NH2:1][CH:2]([CH:14]([CH3:17])[CH2:15][CH3:16])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:4].O.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>O1CCCC1>[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)([OH:28])(=[O:27])=[O:26].[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)([OH:28])(=[O:27])=[O:26].[NH2:1][CH:2]([CH:14]([CH3:17])[CH2:15][CH3:16])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:4]Participants
4
Procedure
To a solution of 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide free base (15 g, 0.062 mol) dissolved in anhydrous tetrahydrofuran (300 mL, 20 vol) was added p-toluenesulfonic acid monohydrate (23.4 g, 0.123 mol, 2 eq) in one portion. The initially clear mixture becomes cloudy and produces a mild exotherm. After about 15 min, crystals begin to precipitate from solution and the mixture continued to stir for 1.5 h. The solids were collected by vacuum filtration, and the wet cake was dried in a 40° C. vacuum oven to afford 32.5 g (90% yield) of 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide Ditosylate as a white solid. 1H NMR confirmed the identity and XRD pattern matches the small scale screen sample pattern.