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Water → (S)-3-((S)-3-(4-(4-tert-butyl-3-isopropylbenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)-4-benzyloxazolidin-2-one

HRID 2235597
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2235597
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([C@H:14]1[CH2:18][O:17][C:16](=[O:19])[N:15]1[C:20](=[O:35])[CH2:21][C@@H:22]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[C:23]1[CH:27]=[CH:26][O:25][N:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:36]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46]Cl)=[CH:42][C:41]=1[CH:48]([CH3:50])[CH3:49])([CH3:39])([CH3:38])[CH3:37].O>CN(C=O)C>[C:36]([C:40]1[CH:45]=[CH:44][C:43]([CH2:46][O:34][C:31]2[CH:32]=[CH:33][C:28]([C@@H:22]([C:23]3[CH:27]=[CH:26][O:25][N:24]=3)[CH2:21][C:20]([N:15]3[C@@H:14]([CH2:7][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:18][O:17][C:16]3=[O:19])=[O:35])=[CH:29][CH:30]=2)=[CH:42][C:41]=1[CH:48]([CH3:50])[CH3:49])([CH3:39])([CH3:38])[CH3:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-oneHCID 593006801-tert-Butyl-4-(chloromethyl)-2-isopropylbenzene

Produkt 1

HCID 67331034(S)-3-((S)-3-(4-(4-tert-butyl-3-isopropylbenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)-4-benzyloxazolidin-2-one
Ausbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Cesium carbonate (360 mg, 1.1 mmol) was added to a mixture of 7.5 (40.0 mg, 0.10 mmol) and 26.5 (27.0 mg, 0.12 mmol) in DMF (2.0 mL). The resulting mixture was stirred at room temperature for 19 hours. The mixture was then treated with water (5 mL) and extracted with EtOAc (15 mL). The organic layer was separated, washed twice with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (0-30% EtOAc/hexane) to give (S)-3-((S)-3-(4-(4-tert-butyl-3-isopropylbenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)-4-benzyloxazolidin-2-one (18.0 mg, 30%) as a clear oil. The ester (18.0 mg, 0.031 mmol) was treated with THF/H2O (3/1, v/v, 2.0 mL) and hydrogen peroxide (30%, 0.021 mL, 0.19 mmol) and cooled to 0° C. LiOH (2.60 mg, 0.062 mmol) was added. The resulting mixture was stirred at 0° C. for 1 hour. A saturated solution of Na2SO3 was added to the mixture, and the reaction was stirred for 1 hour. The mixture was extracted with EtOAc (10 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0-30% EtOAc/hexane) to give 26 (5.80 mg, 44%) as a colorless film. MS ESI (neg.) m/e: 420 (M−H). 1H NMR (500 MHz) (CDCl3) δ 8.28 (1H, s); 7.37-7.34 (2H, m); 7.20-7.17 (3H, m); 6.96-6.94 (2H, d, J=8.2 Hz); 6.07 (1H, s); 4.98 (2H, s); 4.56 (1H, dd, J=7.8, 7.4 Hz); 3.64 (1H, m), 2.36 (1H, dd, J=16.8, 7.8 Hz), 2.99 (1H, dd, J=16.8, 7.4 Hz), 1.43 (9H, s), 1.26 (6H, d, J=7.1 Hz).

Aufarbeitung

  1. extractionextracted with EtOAc (15 mL)
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel (0-30% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0f2b54d976194cb9ac88d85c85898040
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07714008B2

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