Acetone → HCID 131713038、化合物

HRID 1075222ノート

反応式

HRID 1075222 の反応式
[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]

参加物

6

反応物 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

生成物 1

HCID 131713038HCID 131713038、化合物収率 85.6%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8058Hexane溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-5dd6bf63a6664e21a1efcab89d90c552
出典データセット
uspto-grants-1983_07
特許番号
US04395418

反応ノート

読み込み中…