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

HRID 562636
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HRID 562636 반응식
[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6bd2fb839d6e4dd793f9caa1faf0ff32
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067396B2

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