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 259818ノート

反応式

HRID 259818 の反応式
[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

参加物

6

反応物 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

生成物 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]acetamide収率 57%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4ef58245437d4a36be9605774cc6e5b7
出典データセット
uspto-grants-1996_06
特許番号
US05523403

反応ノート

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