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二甲基亚砜 → (3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone

HRID 231237
笔记
打印预览

反应方程式

HRID 231237 反应方程式
FC(F)(F)C(O)=O.CS(C)=O.[Si:12]([N:19]1[C@H:22]([C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C@H:21]([C@H:29]([OH:31])[CH3:30])[C:20]1=[O:32])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O.C(OCC)(=O)C>[C:29]([C@@H:21]1[C@@H:22]([C:23]#[C:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[N:19]([Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:20]1=[O:32])(=[O:31])[CH3:30]
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

8

反应物 4

HCID 679二甲基亚砜HCID 6422三氟乙酸HCID 8471三乙胺HCID 67788869cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone

产物 1

HCID 53923801(3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone收率 32.7%

试剂、催化剂与溶剂 3

HCID 962
聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]
溶剂
HCID 6344二氯甲烷溶剂3 次
HCID 8857乙酸乙酯溶剂

反应条件

温度
-70 °C

实验过程

In an argon stream, a solution of dry trifluoroacetic acid (0.2 ml) in methylene chloride (3 ml) is added dropwise to a mixture of dimethyl sulfoxide (0.1 ml) and methylene chloride (10 ml) at -65° C. or lower, and the mixture is stirred at -70° C. for 0.5 hours. A solution of cis-1-(tert-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.4 g) in methylene chloride (4 ml) is added dropwise at -65° C. or lower and the mixture is stirred at the same temperature for 0.5 hour. After addition of triethylamine (0.3 ml) at the same temperature, the temperature is gradually raised to room temperature. The reaction mixture is poured into a mixture of ethyl acetate (70 ml) and water (100 ml), and the organic layer is separated, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 3% ethyl acetate-97% n-hexane) to give trans i.e. (3S,4S)-3-acetyl-1-(tert-butyldimethylsilyl)-4-trimethylsilylethynyl-2-azetidinone (0.13 g)

后处理

  1. stirringlower and the mixture is stirred at the same temperature for 0.5 hour
  2. temperaturethe temperature is gradually raised to room temperature
  3. customthe organic layer is separated
  4. washwashed with aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

来源与证据

ORD记录
ord-bbcc503110d94085a8f8865eb0323174
来源数据集
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
专利号
US04845210

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记