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Sodium Hydroxide → 3-[4-[(1,1-Dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester

HRID 1647059
ノート
印刷プレビュー

反応式

HRID 1647059 の反応式
S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].[CH2:42]([O:49][C:50](=[O:66])[CH2:51]N=C(C1C=CC=CC=1)C1C=CC=CC=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.Br[CH2:68][C:69]1[CH:81]=[CH:80][C:72]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])=[CH:71][CH:70]=1>ClCCl.CCOCC>[CH2:42]([O:49][C:50](=[O:66])[CH2:51][CH2:68][C:69]1[CH:70]=[CH:71][C:72]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])=[CH:80][CH:81]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 11414578Tert-butyl 4-(bromomethyl)benzoateHCID 11433187Bis(tetrabutylammonium) sulphateHCID 11782449Diphenylmethylene-Glycine benzyl ester

生成物 1

HCID 867465253-[4-[(1,1-Dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester収率 36%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 6344Dichloromethane溶媒

実験手順

Tetrabutyl ammonium sulfate (3.0 g, 9 mmol) was added to a biphasic mixture consisting of 10% aqueous sodium hydroxide (75 mL), 2-[(diphenylmethylene)amino]acetic acid benzyl ester (3.05 g, 9.3 mmol) and 1,1-dimethylethyl 4-bromomethylbenzoate (3.0 g, 9 mmol) in dichloromethane (58 mL). After several hours of vigorous stirring at room temperature, the reaction mixture was diluted with ether (300 mL) and the layers were separated. The organic layer was washed with water (3×30 mL), dried (K2CO3) and filtered. Concentration provided an oil that was purified by HPLC on silica gel (the columns were pre-treated with 10% triethylamine/hexanes, ethyl acetate and finally hexanes) eluting with a mixture of hexanes-ethyl acetate to give rac.-2-](diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester, (1.7 g, 3 mmol) in 36% yield.

後処理

  1. customthe layers were separated
  2. washThe organic layer was washed with water (3×30 mL)
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationConcentration
  6. customprovided an oil that
  7. customwas purified by HPLC on silica gel (the columns
  8. additionwere pre-treated with 10% triethylamine/hexanes, ethyl acetate and finally hexanes)
  9. washeluting with a mixture of hexanes-ethyl acetate

出典と根拠

ORDレコード
ord-64e2a740e9364e50820298a4b8d45b2d
出典データセット
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05182263

反応ノート

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