Acetone → HCID 131713038, 화합물

HRID 1075222노트

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HRID 1075222 반응식
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([S:15][C:16]([S:18][C@H:19]([CH3:35])[CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])=[S:17])[NH:13][C:12]1=[O:36])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.[C:38]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=1)(=[O:41])[CH:39]=[O:40].CC(C)=O>C1C=CC=CC=1.CCCCCC>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([S:15][C:16]([S:18][C@H:19]([CH3:35])[CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)=[O:23])=[S:17])[N:13]([CH:39]([OH:40])[C:38]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([N+:50]([O-:52])=[O:51])=[CH:48][CH:49]=2)=[O:41])[C:12]1=[O:36])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 180AcetoneHCID 21934455p-Nitrobenzyl glyoxylate hydrateHCID 57296186(3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-2-(p-nitrobenzyloxycarbonylamino)ethylthio(thiocarbonyl)]thioazetidin-2-one

생성물 1

HCID 131713038HCID 131713038, 화합물수율 85.6%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8058Hexane용매

실험 절차

(3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-2-(p-nitrobenzyloxycarbonylamino)ethylthio(thiocarbonyl)]thioazetidin-2-one (10.8 g, 18.8 mmole) and p-nitrobenzyl glyoxylate hydrate (8.53 g, 37.6 mmole) were refluxed in benzene (100 ml) for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was purified by column chromatography (150 g of silica gel), eluted first with a 15% v/v solution of acetone in hexane, giving some unchanged starting compound (1.62 g, 15%), and then with a 30% v/v solution of acetone in hexane, giving the desired compound (12.6 g, 85%) in the form of a yellow oil.

후처리

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by column chromatography (150 g of silica gel)
  4. washeluted first with a 15% v/v solution of acetone in hexane
  5. customgiving

출처 및 근거

ORD 기록
ord-5dd6bf63a6664e21a1efcab89d90c552
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04395418

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