Dimethyl Sulfate → (R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamide

HRID 74117Notes

Reaction equation

HRID 74117 reaction equation
[CH2:1]([NH:8][C:9](=[O:19])[C@H:10]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](OCC)(=O)C.S(OC)(OC)(=O)=O.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([NH:8][C:9](=[O:19])[C@H:10]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][O:12][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 53344986(R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide

Product 1

HCID 53344987(R)-N-benzyl-2-(ethoxycarbonylamino)-3-methoxypropionamideYield 70.96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a 500 mL three-neck round bottom flask, 7.2 g (0.027 mol) (R)-N-benzyl-2-(ethoxycarbonylamino)-3-hydroxypropionamide, 300 mL ethyl acetate, 27.2 g (0.216 mol) dimethyl sulfate, and 2.0 g tetrabutylammonium bromide were added in sequence. At a normal temperature, 24.8 g 50% potassium hydroxide (0.2214 mol) solution was added. After the reaction was completed, 100 mL water was added, and the mixture was stirred for several minutes, and stood for layering. An organic layer was separated, and washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated, to obtain a transparent oily substance, which was triturated with n-hexane, suction-filtered, washed, and dried, to obtain a white solid of 5.37 g (0.01916 mol). The molar yield was 70.96%.

Workup

  1. customAn organic layer was separated
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto obtain a transparent oily substance, which
  6. customwas triturated with n-hexane
  7. filtrationsuction-filtered
  8. washwashed
  9. customdried
  10. customto obtain a white solid of 5.37 g (0.01916 mol)

Sources & evidence

ORD record
ord-97cd46039495446584bca2082a5cf2de
Source dataset
uspto-grants-2014_09
Patent number
US08829226B2

Reaction notes

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