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Ammonium Chloride → (2R)-2-t-Butoxycarbonylamino-2-ethyl-1-n-hexanoyloxy-4-(furan-2-yl)-3-butene

HRID 422934
ノート
印刷プレビュー

反応式

HRID 422934 の反応式
[Br-].[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:33]([O:37][C:38]([NH:40][C@@:41]([CH2:53][CH3:54])([CH2:44][O:45][C:46](=[O:52])[CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH:42]=O)=[O:39])([CH3:36])([CH3:35])[CH3:34].[Cl-].[NH4+]>O1CCCC1>[C:33]([O:37][C:38]([NH:40][C@:41]([CH2:53][CH3:54])([CH:42]=[CH:7][C:3]1[O:2][CH:6]=[CH:5][CH:4]=1)[CH2:44][O:45][C:46](=[O:52])[CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:39])([CH3:35])([CH3:36])[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 11418806Furfuryltriphenylphosphonium bromideHCID 20721240(2S)-2-t-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanalHCID 23665647Potassium tert-butoxide

生成物 1

HCID 66672873(2R)-2-t-Butoxycarbonylamino-2-ethyl-1-n-hexanoyloxy-4-(furan-2-yl)-3-butene収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of (furan-2-yl)methyl triphenylphosphonium bromide (4.04 g, 9.54 mmol) obtained in Reference example 1 in tetrahydrofuran (32.4 ml) was added potassium t-butoxide (1.06 g, 9.45 mmol) with stirring under ice-cooling, and the resulting mixture was furthermore stirred under ice-cooling for 15 minutes. After stirring, to the reaction mixture was added a solution of (2S)-2-t-butoxycarbonylamino-2-ethyl-3-n-hexanoyloxy-1-propanal (2.01 g, 6.37 mmol) obtained in Reference example (14b) in tetrahydrofuran (10 ml) with stirring under ice-cooling over a 5-minute interval, and the resulting mixture was furthermore stirred under ice-cooling for 30 minutes. After stirring, saturated aqueous ammonium chloride solution was added to the reaction mixture to quench the reaction, and the reaction temperature was raised to room temperature. After evaporation of the reaction mixture in vacuo, ethyl acetate and water were added to the residue, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (5:1) as the eluent to afford the title compound (2.385 g, yield: 99%).

後処理

  1. temperaturecooling
  2. stirringthe resulting mixture was furthermore stirred under ice-
  3. temperaturecooling for 15 minutes
  4. stirringAfter stirring, to the reaction mixture
  5. stirringwith stirring under ice-
  6. temperaturecooling over a 5-minute interval
  7. stirringthe resulting mixture was furthermore stirred under ice-
  8. temperaturecooling for 30 minutes
  9. stirringAfter stirring
  10. customto quench
  11. customthe reaction
  12. customAfter evaporation of the reaction mixture in vacuo, ethyl acetate and water
  13. additionwere added to the residue
  14. extractionthe resulting mixture was extracted with ethyl acetate
  15. washThe extract was washed with saturated aqueous sodium chloride solution
  16. dry with materialdried over anhydrous sodium sulfate
  17. filtrationAfter filtration
  18. customthe solvent was removed in vacuo
  19. customthe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-e46ed41a579a48fe8d6db021da1c3647
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08101650B2

反応ノート

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