Imidazole → (3S,4S)-N-[(tert-Butyloxy)-carbonyl]-4-amino-5-phenyl-3-(triisopropylsilyloxy)-pentene

HRID 6075

Reaktionsgleichung

Reaktionsgleichung von HRID 6075
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@@H:10]([OH:13])[CH:11]=[CH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.Cl[Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29].O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C@@H:10]([O:13][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH:11]=[CH2:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 10468747(3S,4S)-4-(t-Butyloxycarbonylamino)-3-hydroxy-5-phenyl-1-pentene

Produkt 1

HCID 15281981(3S,4S)-N-[(tert-Butyloxy)-carbonyl]-4-amino-5-phenyl-3-(triisopropylsilyloxy)-penteneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (3S,4S)-N-[(tertbutyloxy)carbonyl]-4-amino-3-hydroxy-5-phenyl pentene [prepared by the method of Hanson et al, J. Org. Chem., 50, 5399 (1985)] (10.0 g, 64.5 mmol), imidazole (9.14g, 13 mmol), and chlorotriisopropylsilane (12.44 g, 43.3 mmol) in anhydrous DMF (40 mL) was stirred for 5 days at room temperature under an N2 atmosphere. The solution was poured into H2O (500 mL) and extracted with Et2O (2×25 mL). The combined organic layers were washed with H2O (250 mL), a 0.5M citric acid solution (2×120 mL), a 5% KHCO3 solution (2×100 mL), and brine (2×100 mL). After the organic layer was dried over MgSO4, the filtrate was concentrated and purified by medium pressure column chromatography (silica gel, 10% ethyl acetate in hexane, Rf 0.23) to give 12.9 g (82 % yield) of the title compound as a clear, colorless oil. 1H and 13C NMR spectral data were consistent with the proposed structure.

Aufarbeitung

  1. extractionextracted with Et2O (2×25 mL)
  2. washThe combined organic layers were washed with H2O (250 mL)
  3. dry with materialAfter the organic layer was dried over MgSO4
  4. concentrationthe filtrate was concentrated
  5. custompurified by medium pressure column chromatography (silica gel, 10% ethyl acetate in hexane, Rf 0.23)

Quellen und Nachweise

ORD-Eintrag
ord-0892ced2a4104a93b742dbf72a8cc112
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246969

Verknüpfte Notizen

Wird geladen…