5-Bromo-2-methoxycyclohepta-2,4,6-trien-1-one → (S)-N-[[3-[3-fluoro-4-(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 259818노트

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HRID 259818 반응식
[I-].O1CCNC1=O.[F:8][C:9]1[CH:10]=[C:11]([N:19]2[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:12]=[CH:13][C:14]=1[Sn](C)(C)C.Br[C:31]1[CH:37]=[CH:36][C:35](=[O:38])[C:34]([O:39][CH3:40])=[CH:33][CH:32]=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:8][C:9]1[CH:10]=[C:11]([N:19]2[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:12]=[CH:13][C:14]=1[C:31]1[CH:37]=[CH:36][C:35](=[O:38])[C:34]([O:39][CH3:40])=[CH:33][CH:32]=1

참가 물질

6

반응물 3

HCID 6040175-Bromo-2-methoxycyclohepta-2,4,6-trien-1-oneHCID 11304566N-({(5S)-3-[3-Fluoro-4-(trimethylstannyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamideHCID 21585223Oxazolidinone iodide

생성물 1

HCID 44264058(S)-N-[[3-[3-fluoro-4-(4-methoxy-5-oxo-1,3,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide수율 57%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Alternatively, the oxazolidinone iodide described above can be converted to (S)-N-[[3-[3-fluoro-4-(trimethylstannyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, employing conditions disclosed for the corresponding racemic material in TR 7246-92-050. This tin-substituted intermediate (0.180 g, 0.43 mmol) and 5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one (0.103 g, 0.48 mmol) were dissolved in dry DMF (3 mL) and the resultant solution degassed by repeated evacuation and filling with nitrogen. Bis(triphenylphosphine)palladium(II) chloride (0.015 g, 0.02 mmol) was added, the reaction again degassed, and the mixture heated to 80° C. for 2 h. TLC revealed some starting material still remained, so additional palladium catalyst (0.015 g) was added and the mixture heated a further 5 h. The reaction mixture was concentrated in vacuo and the residue chromatographed over silica gel, eluting with a methanol/chloroform gradient, to afford 0.096 g (57%) of the title compound, identical in all respects to material prepared via the above protocol.

후처리

  1. customthe resultant solution degassed
  2. customthe reaction
  3. customagain degassed
  4. additionso additional palladium catalyst (0.015 g) was added
  5. temperaturethe mixture heated a further 5 h
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customthe residue chromatographed over silica gel
  8. washeluting with a methanol/chloroform gradient

출처 및 근거

ORD 기록
ord-4ef58245437d4a36be9605774cc6e5b7
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523403

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