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Sodium hydride → (R)-Methyl 2-(((2-((tert-butoxycarbonyl)amino)pent-4-en-1-yl)oxy)methyl)benzoate

HRID 1429380
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1429380
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH2:11][CH:12]=[CH2:13])[CH2:9][O:10][CH2:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[O:14])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 11106388Carbamic acid, [(1R)-1-(hydroxymethyl)-3-butenyl]-, 1,1-dimethylethyl ester

Produkt 1

HCID 68233281(R)-Methyl 2-(((2-((tert-butoxycarbonyl)amino)pent-4-en-1-yl)oxy)methyl)benzoateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of compound 18g (6.2 g, 30.8 mmol) and compound 18c (8.5 g, 36.9 mmol) in THF (30 mL) was cooled in an ice bath under argon. To this mixture was added NaH (2.5 g, 61.6 mmol, 60% wt in oil) portionwise. The ice bath was removed and the reaction mixture was allowed to stir at rt for 2 h and then quenched with MeOH (10 mL). The mixture was concentrated under reduced pressure and the residue was purified by CC to give the desired compound 18h (4.2 g, 39% yield) as a yellow oil. LCMS (m/z): 350.2 (MH+).

Aufarbeitung

  1. customThe ice bath was removed
  2. customquenched with MeOH (10 mL)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by CC

Quellen und Nachweise

ORD-Eintrag
ord-e735fed5baa0455bb0e59d5f787a7820
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08940722B2

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