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2,3-Dihydroxybutanedioic Acid → 3-(5-(Tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-2-[(4-fluorophenyl-amino)-(4-hydroxyphenyl)methyl]pentanoyl)-4-phenyloxazolidin-2-one

HRID 2104915
ノート
印刷プレビュー

反応式

HRID 2104915 の反応式
[Si:1]([O:8][CH:9]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH2:10][CH2:11][CH2:12][C:13]([N:15]1[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][O:17][C:16]1=[O:26])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:34][C:35]1[CH:40]=[CH:39][C:38]([N:41]=[CH:42][C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)=[CH:37][CH:36]=1.C(N(C(C)C)C(C)C)C.C[Si](Cl)(C)C.C(O)(=O)C(C(C(O)=O)O)O.S([O-])(O)=O.[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C>[Si:1]([O:8][CH:9]([C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)[CH2:10][CH2:11][CH:12]([CH:42]([NH:41][C:38]1[CH:39]=[CH:40][C:35]([F:34])=[CH:36][CH:37]=1)[C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1)[C:13]([N:15]1[CH:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][O:17][C:16]1=[O:26])=[O:14])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 6

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6397ChlorotrimethylsilaneHCID 81531DiisopropylethylamineHCID 7202544-[[(4-Fluorophenyl)imino]methyl]phenolHCID 121116183-[5-(tert-Butyldimethylsilanyloxy)-5-(4-fluorophenyl)pentanoyl]4-phenyloxazolidin-2-oneHCID 23665763Sodium Bisulfite

生成物 1

HCID 222520473-(5-(Tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)-2-[(4-fluorophenyl-amino)-(4-hydroxyphenyl)methyl]pentanoyl)-4-phenyloxazolidin-2-one

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

10 g of 3-[5-(tert-butyldimethylsilanyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyloxazolidin-2-one are dissolved in 80 ml of absolute dichlormethane. 9.12 g of 4-[(4-fluorophenylimino)methyl]phenol and 19.6 ml of ethyldiisopropylamine are added, and the solution is then cooled to −10° C. 6.7 ml of trimethylsilyl chloride are then added dropwise, the temperature of the reaction mixture being maintained at below −5° C. The reaction solution is stirred at −10° C. for half an hour and then cooled to −30° C., and 2.7 ml of titanium tetrachloride are added dropwise, the temperature being maintained between −30° C. and −15° C. This gives a black reaction solution which is stirred at −20° C. for another 3 h and then allowed to warm to 0° C. In the stated order, in intervals of 10 minutes, 6 ml of glacial acetic acid, 60 ml of 7% strength aqueous tartaric acid solution and finally 100 ml of 20% strength aqueous sodium hydrogensulfite solution are then added with stirring. The mixture is then extracted three times with dichloromethane and the organic phase is washed once with saturated sodium chloride solution and dried over sodium sulfate. The solvent is removed using a rotary evaporator and the residue is purified by column chromatography (SiO2; ethyl acetate/heptane 1:4). The product is obtained from diethyl ether/pentane as white crystals. C39H44F2N2O5Si (686) MS (ESI): M+-241

後処理

  1. temperaturethe temperature of the reaction mixture being maintained at below −5° C
  2. temperaturecooled to −30° C.
  3. temperaturethe temperature being maintained between −30° C. and −15° C
  4. customThis gives a black reaction solution which
  5. stirringis stirred at −20° C. for another 3 h
  6. temperatureto warm to 0° C
  7. stirringwith stirring
  8. extractionThe mixture is then extracted three times with dichloromethane
  9. washthe organic phase is washed once with saturated sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. customThe solvent is removed
  12. customa rotary evaporator
  13. customthe residue is purified by column chromatography (SiO2; ethyl acetate/heptane 1:4)
  14. customThe product is obtained from diethyl ether/pentane as white crystals

出典と根拠

ORDレコード
ord-1c211c55e6fd405a944f1cf838f25494
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576200B2

反応ノート

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