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Imidazole → tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 16329
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16329
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[C:24]([O:28][C:29](=[O:44])[NH:30][C@H:31]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C@H:32]([OH:34])[CH3:33])([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>O.C(OCC)(=O)C>[C:24]([O:28][C:29](=[O:44])[NH:30][C@H:31]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C@H:32]([O:34][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:33])([CH3:25])([CH3:26])[CH3:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

Produkt 1

HCID 68718850tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In nitrogen atmosphere, tert-butyldiphenylsilyl chloride (2.0 mL) was added dividedly four times to a DMF solution (3 mL) of [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]-carbamic acid tert-butyl ester (610 mg) and imidazole (817 mg). This reaction solution was stirred at room temperature for 3 hr. To the reaction solution, ethyl acetate and water were added. The organic layer was separated, washed with 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane:diethylether=49:1 to 19:1) to give 684 mg of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with 1 N hydrochloric acid, water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: hexane:diethylether=49:1 to 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-cbe249a5d1264e269f037a95cd7c9cbc
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737141B2

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