Potassium Carbonate → 2-(4-(2,3-Epoxypropoxy)phenyl)acetamide

HRID 2288262Notes

Reaction equation

HRID 2288262 reaction equation
[CH:1]1[C:6]([CH2:7][C:8]([NH2:10])=[O:9])=[CH:5][CH:4]=[C:3]([OH:11])[CH:2]=1.C1(C)C=CC(S(O[CH2:22][C@H:23]2[O:25][CH2:24]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:11][CH2:22][CH:23]2[O:25][CH2:24]2)=[CH:2][CH:1]=1)(=[O:9])[NH2:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86986(4-Hydroxyphenyl)acetamideHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Product 1

HCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Hydroxyphenylacetamide (1 g) and (S)-glycidyl p-toluenesulfonate (1.51 g, 99.3% e.e.) were dissolved in acetone (30 ml). Potassium carbonate (1.19 g) was added to the solution and the solution was stirred for 30 hours under refluxing. After the reaction, inorganic materials were filtered off and acetone was removed to give 1.43 g of crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane. The optical purity of it was 62.8% e.e. by measurement of Chiral column OD (Daisel Chemical industries Ltd.).

Workup

  1. temperatureunder refluxing
  2. customAfter the reaction, inorganic materials
  3. filtrationwere filtered off
  4. customacetone was removed

Sources & evidence

ORD record
ord-5e84bf6ba699449b9bf5ae02fd5e6c11
Source dataset
uspto-grants-2000_07
Patent number
US06087512

Reaction notes

Loading…