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

HRID 1107056Notes

Reaction equation

HRID 1107056 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 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. Then, crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane (1.43 g) was dissolved in methanol (8 ml). The solution was dropped in isopropylamine (6.8 g) under cooling to 10° C. over a period of 1 hour and the reaction temperature was raised to room temperature and stirred for 7 hours. After the reaction, the mixture was condensed in vacuo until crystals beginning to separate, cooled, filtrated by suction and dried in vacuo to give crude (S)-atenolol (1.29 g). 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-625060aa6a274a8abc672ff94ec3ceda
Source dataset
uspto-grants-2000_05
Patent number
US06057476

Reaction notes

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