Trimethylsilyl triflate → HCID 88672369、化合物

HRID 342301ノート

反応式

HRID 342301 の反応式
C([O:4][C@H:5]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:7](=O)[C@H:6]1[C@H:19]([O:21][C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH3:20])(=O)C.[C:28]1([S:34][C:35]([O:37][Si](C)(C)C)=[CH2:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:25]([O:24][C:22]([O:21][C@@H:19]([C@@H:6]1[C@@H:7]([CH2:36][C:35]([S:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:37])[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]1=[O:4])[CH3:20])=[O:23])[CH:26]=[CH2:27]

参加物

6

反応物 3

HCID 65367Trimethylsilyl triflateHCID 11447442Silane, trimethyl[[1-(phenylthio)ethenyl]oxy]-HCID 70450099HCID 70450099、化合物

生成物 1

HCID 88672369HCID 88672369、化合物収率 91.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 377 mg of (3S, 4R)-4-acetoxy-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-1-(p-methoxybenzyl)-2-azetidinone in 2 ml of dry methylene chloride were added 448 mg (2 mmole) of 1-phenylthio-1-(trimethylsilyloxy)ethylene and then the mixture was stirred at room temperature, A catalytic amount of trimethylsilyltrifluoromethanesulphonate was added to the mixture, which was then left to stand at room temperature overnight. The precipitate produced was dissolved in 200 ml of ethyl acetate, and the resulting solution was washed successively with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride. It was then dried over anhydrous magnesium sulphate and subjected to Lobar column chromatography eluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate, to afford 430 mg (yield 91%) of the title azetidinone.

後処理

  1. waitwas then left
  2. customThe precipitate produced
  3. washthe resulting solution was washed successively with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialIt was then dried over anhydrous magnesium sulphate
  5. washeluted with a 1:1 by volume mixture of cyclohexane and ethyl acetate

出典と根拠

ORDレコード
ord-6ffa115e09004e3f97cddb248a87bf03
出典データセット
uspto-grants-1999_01
特許番号
US05856556

反応ノート

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