p-Toluenesulfonic acid monohydrate → 3-methoxy-2-methoxymethyl-2-methyl-N-(3-oxo-propyl)-propionamide

HRID 220259Notes

Reaction equation

HRID 220259 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

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86641927N-(3,3-diethoxy-propyl)-3-methoxy-2-methoxymethyl-2-methyl-propionamide

Product 1

HCID 866419283-methoxy-2-methoxymethyl-2-methyl-N-(3-oxo-propyl)-propionamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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

Workup

  1. customquenched with sat.-NaHCO3
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anh. Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude material was purified by CC

Sources & evidence

ORD record
ord-5366c34f39d048ba86ae05cff406bbab
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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