Potassium Carbonate → (S)-N-(4-methoxyphenyl)-2-methyloxirane-2-carboxamide

HRID 1694772Notes

Reaction equation

HRID 1694772 reaction equation
Br[CH2:2][C@@:3]([OH:16])([CH3:15])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:4]([C@:3]2([CH3:15])[CH2:2][O:16]2)=[O:5])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67280255(R)-3-bromo-2-hydroxy-N-(4-methoxyphenyl)-2-methylpropanamide

Product 1

HCID 86616421(S)-N-(4-methoxyphenyl)-2-methyloxirane-2-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(R)-3-bromo-2-hydroxy-N-(4-methoxyphenyl)-2-methylpropanamide (6b) (5.80 g, 20.13 mmol) and K2CO3 (5.56 g, 40.26 mmol) were placed in a 500 mL round-bottomed flask fitted with a stirring bar. 150 mL of acetone was added at room temperature. The reaction solution was heated to reflux for 3 hours. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (silica gel, EtOAc/hexanes=1/1 v/v) to give a white solid product, (S)—N-(4-methoxyphenyl)-2-methyloxirane-2-carboxamide, 4.00 g, 96.0% yield.

Workup

  1. customfitted with a stirring bar
  2. temperatureThe reaction solution was heated
  3. temperatureto reflux for 3 hours
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, EtOAc/hexanes=1/1 v/v)

Sources & evidence

ORD record
ord-04ace802b34247c398fab8de63245233
Source dataset
uspto-grants-2012_04
Patent number
US08158828B2

Reaction notes

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