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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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
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HRID 1464727 반응식
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]
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참가 물질

5

반응물 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

생성물 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
수율 13.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)]

출처 및 근거

ORD 기록
ord-d55ebd7ade194739b74ddbf9298093cb
출처 데이터셋
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05306816

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