Imidazole → HCID 89463962, Verbindung

HRID 2275399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275399
[NH2:1][C@@H:2]([CH2:13][OH:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl.C1COCC1>[Si:20]([O:14][CH2:13][C@H:2]([NH2:1])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734051(2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol

Produkt 1

HCID 89463962HCID 89463962, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of D-Tryptophanol (1.024 g) and imidazole (403 mg) in DCM (40 ml) and THF (8 ml) was added a solution of tert-butyldimethylsilyl chloride (0.852 g) in DCM (5 ml) dropwise. The reaction was allowed to warm to room temperature overnight. The reaction mixture was quenched with a saturated aqueous NaHCO3 solution and the reaction mixture was extracted with dichloromethane. The aqueous phase was washed with dichloromethane and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with heptane and increasing amounts of ethyl acetate.

Aufarbeitung

  1. customThe reaction mixture was quenched with a saturated aqueous NaHCO3 solution
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washThe aqueous phase was washed with dichloromethane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel eluting with heptane
  9. temperatureincreasing amounts of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-059d5a59b302476a9e39b9efbd389193
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09127007B2

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