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Diisopropylamine → benzyl (2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate

HRID 546684
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HRID 546684 반응식
C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:15]=[C:16]([CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH:17]=[C:18]([F:21])[C:19]=1[F:20].[O:33]([CH2:51][CH2:52][CH2:53][OH:54])[Si:34]([C:47]([CH3:50])([CH3:49])[CH3:48])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Si:34]([O:33][CH2:51][CH2:52][C@@H:53]([OH:54])[C@H:22]([C:16]1[CH:15]=[C:14]([F:13])[C:19]([F:20])=[C:18]([F:21])[CH:17]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])([C:47]([CH3:49])([CH3:50])[CH3:48])([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1.[Si:34]([O:33][CH2:51][CH2:52][C@H:53]([OH:54])[C@H:22]([C:16]1[CH:15]=[C:14]([F:13])[C:19]([F:20])=[C:18]([F:21])[CH:17]=1)[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])([C:47]([CH3:49])([CH3:50])[CH3:48])([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 102451343-(Tert-butyldiphenylsiloxy)propanolHCID 86628508Benzyl (3,4,5-trifluorophenyl)acetateHCID 178418339Butyllithium

생성물 2

HCID 66838983benzyl (2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate
HCID 66839318benzyl (2S*,3S*)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

n-Butyl lithium (1.82 mL; 2.66 M solution in hexane) was added dropwise to a solution of diisopropylamine (0.735 mL) in THF (6 mL) at 0° C. The reaction solution was stirred at 0° C. for 20 minutes and then cooled to −78° C. Benzyl (3,4,5-trifluorophenyl)acetate (1.13 g) in THF (18 mL) was added dropwise to the reaction solution, and the reaction solution was stirred at −78° C. for 15 minutes. Thereafter, 3-(tert-butyldiphenylsiloxy)propanol (CAS No. 112897-03-7, 1.26 g) in THF (6 mL) was added dropwise to the reaction solution, and the reaction solution was stirred at −78° C. for 30 minutes. A saturated ammonium chloride solution was added to the reaction solution, and the reaction solution was returned to room temperature. Ethyl acetate was added and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 840 mg of benzyl (2S*,3R*)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate and 765 mg of benzyl (2S*,3S*)-5-(tert-butyldiphenylsilanyloxy)-3-hydroxy-2-(3,4,5-trifluorophenyl)pentanoate.

후처리

  1. temperaturecooled to −78° C
  2. stirringthe reaction solution was stirred at −78° C. for 15 minutes
  3. stirringthe reaction solution was stirred at −78° C. for 30 minutes
  4. customwas returned to room temperature
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-5341a4c9430947c08ea7dd838ffcb6a4
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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