Benzyl Bromide → (3S,4S)-4-(1-benzyloxycarbonylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

HRID 1196201Notes

Reaction equation

HRID 1196201 reaction equation
[C:1]([C:4]([C@H:6]1[N:9]([CH:10]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:8](=[O:29])[C@@H:7]1[C@H:30]([O:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH3:31])=[CH2:5])([OH:3])=[O:2].[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:43]([O:2][C:1]([C:4]([C@H:6]1[N:9]([CH:10]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[C:8](=[O:29])[C@@H:7]1[C@H:30]([O:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH3:31])=[CH2:5])=[O:3])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67919435(3S,4S)-4-(1-carboxyethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Product 1

HCID 67919445(3S,4S)-4-(1-benzyloxycarbonylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (3S,4S)-4-(1-carboxyethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (3.7 g) in acetone (60 ml) was treated with benzyl bromide (1.4 g) in the presence of anhydrous potassium carbonate (1.88 g) under reflux for 2 hours. The reaction mixture was cooled down to room temperature, filtered to remove insoluble materials and concentrated in vacuo. The concentrate was diluted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-benzyloxycarbonylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationfiltered
  3. customto remove insoluble materials
  4. concentrationconcentrated in vacuo
  5. additionThe concentrate was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-8fecda6a72b14d9386f34fc2b6e0e354
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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