p-Toluenesulfonic acid monohydrate → 2-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide Ditosylate

HRID 918894Notes

Reaction equation

HRID 918894 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

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 119593722-amino-3-methyl-N-[2-(morpholin-4-yl)ethyl]pentanamide

Product 1

HCID 866754812-amino-3-methyl-N-(2-morpholinoethyl)-pentanamide DitosylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customproduces a mild exotherm
  2. customto precipitate from solution
  3. filtrationThe solids were collected by vacuum filtration
  4. customthe wet cake was dried in a 40° C. vacuum oven

Sources & evidence

ORD record
ord-d5c6438016eb415aa820d5c3f6964a6f
Source dataset
uspto-grants-2016_03
Patent number
US09271986B2

Reaction notes

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