Benzyl Bromide → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate

HRID 1006084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006084
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([O:14][C:13](=[O:15])[C@@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

Produkt 1

HCID 11243734(R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoateAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-Tert-butoxycarbonyl-D-valine (70 g, 0.32 mol) and cesium carbonate (200.2 g, 0.615 mol) were stirred in dry dimethylformamide (550 mL). Benzyl bromide (40.32 mL, 0.336 mol) was added and the reaction mixture was stirred overnight. The material was concentrated on the roto-evaporator and the residue was dissolved in methylene chloride (200 mL) and the methylene chloride layer was washed with water and brine, dried over magnesium sulfate and concentrated to give N-tert-butoxycarbonyl-D-valine benzyl ester (97 g) as a viscous oil.

Aufarbeitung

  1. concentrationThe material was concentrated on the roto-evaporator
  2. dissolutionthe residue was dissolved in methylene chloride (200 mL)
  3. washthe methylene chloride layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a5860a393df543f5b9d1d59b4af726af
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787559B2

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