Dicyclohexylcarbodiimide → N,2-Dimethoxy-N,2-dimethylpropanamide

HRID 1677435Notes

Reaction equation

HRID 1677435 reaction equation
[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=O.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:24][O:25][NH:26][CH3:27]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([N:26]([O:25][CH3:24])[CH3:27])=[O:6]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14232N,O-DimethylhydroxylamineHCID 98554652-methoxy-2-methylpropanoic acid

Product 1

HCID 86646687N,2-Dimethoxy-N,2-dimethylpropanamideYield 14.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methoxy-2-methyl-propionic acid (1.0 g, 8.46 mmol) in anhydrous dichloromethane (10 ml) was slowly treated with DCC (1M in DCM, 10.16 ml, 10.16 mmol), O,N-Dimethyl-hydroxylamine (991 mg, 10.16 mmol), DMAP (103 mg, 0.843 mmol), and TEA (1.42 ml, 10.16 mmol). The reaction mixture was allowed to stir at room temperature for 16 hours. The reaction mixture was partitioned between DCM/1N HCl. The organic layers were collected, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography using 5-60% EtOAc in hexanes as eluant providing 200 mg (14.66%) of 2,N-dimethoxy-2,N-dimethyl-propionamide as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between DCM/1N HCl
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6b14b86409254ae69e61daaa24b2366a
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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