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

HRID 1196201노트

반응식

HRID 1196201 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8fecda6a72b14d9386f34fc2b6e0e354
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112966

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