ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Triethyl phosphite → allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464727
ノート
印刷プレビュー

反応式

HRID 1464727 の反応式
P(OCC)(OCC)OCC.[CH2:11]([O:14][C:15](=[O:39])[C:16]([N:18]1[C@H:21]([C@H:22]([C:24]([S:26][CH3:27])=S)[CH3:23])[C@@H:20]([C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH3:29])[C:19]1=[O:38])=O)[CH:12]=[CH2:13].C(OC(=O)C(N1[C@H]([C@@H](C(SC)=S)C)[C@@H]([C@H](O[Si](C(C)(C)C)(C)C)C)C1=O)=O)C=C>C1(C)C=CC=CC=1>[Si:31]([O:30][C@@H:28]([C@H:20]1[C:19](=[O:38])[N:18]2[C@@H:21]1[C@@H:22]([CH3:23])[C:24]([S:26][CH3:27])=[C:16]2[C:15]([O:14][CH2:11][CH:12]=[CH2:13])=[O:39])[CH3:29])([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:32])[CH3:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 31215Triethyl phosphiteHCID 86747781(3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidineHCID 86747782(3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

生成物 1

HCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
収率 13.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of triethyl phosphite (1.43 g), toluene (3 ml) and a mixture (1.0 g) of (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-1-(allyloxyoxalyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1S)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine was heated at 80° C. for 26 hours and then refluxed for 16 hours. After removal of the solvent, the residue was dissolved in hexane, washed with water, dried, and concentrated in vacuo. The oily residue was purified by silica gel column chromatography [diethyl ether-hexane (1:3, V/V)] to afford a mixture (118 mg) of allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and allyl (4S,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3 -methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

後処理

  1. temperaturerefluxed for 16 hours
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in hexane
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by silica gel column chromatography [diethyl ether-hexane (1:3, V/V)]

出典と根拠

ORDレコード
ord-d55ebd7ade194739b74ddbf9298093cb
出典データセット
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05306816

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート