Ethyl Acetate → 1-(alpha-Benzyloxycarbonylbenzyl)-3-(2-phenyl)acetamido-2-azetidinone

HRID 1706512Notes

Reaction equation

HRID 1706512 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH2:14][NH:13][C:12]2=[O:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:17]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].[H-].[Na+].C(OCC)(=O)C>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:21]([O:20][C:18]([CH:17]([N:13]1[CH2:14][CH:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:15])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 132120483-[(Phenylacetyl)amino]-2-azetidinoneHCID 20445638Benzyl 2-bromo-2-phenylacetate

Product 1

HCID 155923161-(alpha-Benzyloxycarbonylbenzyl)-3-(2-phenyl)acetamido-2-azetidinone

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-Phenylacetamido)-2-azetidinone (816 mg.) and benzyl 2-bromo-2-phenylacetate (1.22 g.) were dissolved in N,N-dimethylformamide (20 ml.), and to the solution was added sodium hydride (50% oily) (210 mg.) in nitrogen atmosphere under ice-cooling while stirring, and then the reaction mixture was stirred for an hour at the same temperature. Ethyl acetate (150 ml.) was added to the reaction mixture, and the solution was washed with water, a sodium bicarbonate-saturated-aqueous solution and water respectively, and then dried over anhydrous magnesium sulfate. The solution was evaporated to dryness under reduced pressure to give the yellow oily material (1.7 g.). The material was subjected to column chromatography using silica.gel (developer: chloroform) to give two isomers of 1-(α-benzyloxycarbonylbenzyl)-3-(2-phenyl)acetamido-2-azetidinone. Yield of the isomer A is 26 mg. and it of the isomer B is 65 mg.

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred for an hour at the same temperature
  3. washthe solution was washed with water
  4. dry with materiala sodium bicarbonate-saturated-aqueous solution and water respectively, and then dried over anhydrous magnesium sulfate
  5. customThe solution was evaporated to dryness under reduced pressure
  6. customto give the yellow oily material (1.7 g.)

Sources & evidence

ORD record
ord-40da6923c7ba467aa3c9fc528154593e
Source dataset
uspto-grants-1980_06
Patent number
US04207234

Reaction notes

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