Imidazole → HCID 57947507, Verbindung

HRID 409766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409766
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][OH:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C(OCC)C>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:17][O:18][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 57947757HCID 57947757, Verbindung

Produkt 1

HCID 57947507HCID 57947507, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of (S)-methyl 5-(tert-butoxycarbonylamino)-6-hydroxyhexanoate (12 g, 46 mmol) in DMF (100 mL) was added imidazole (7.8 g, 115 mmol, 2.5 equiv.). TBS-Cl (8.25 g, 55 mmol, 1.2 equiv.) was then added in 3 portions. The reaction was complete in 30 min. Diethyl ether (200 mL) and brine (300 mL) were added to the reaction solution. The organic layer was further washed with brine (300 mL), dried, and concentrated to give (S)-methyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldimethylsilyloxy)hexanoate (15.9 g, 92%) as a colorless oil. LRMS (M−Boc+H+) m/z 276.1.

Aufarbeitung

  1. washThe organic layer was further washed with brine (300 mL)
  2. customdried
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-89d829ef31ef4b6bafd7bf384e91a389
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759374B2

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