Imidazole → (R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

HRID 1254340

Reaktionsgleichung

Reaktionsgleichung von HRID 1254340
[CH3:1][O:2][C:3]([C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:6][OH:7])=[O:4].N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:6][O:7][Si:25]([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26])=[O:4]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 377723N-Boc-D-serine methyl ester

Produkt 1

HCID 10860583(R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoateAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (R)-1-(methoxycarbonyl)-2-hydroxyethylcarbamate (27.5 g, 0.126 mol) in DMF (250 mL) was added imidazole (25.7 g, 0.378 mol), followed by TBSCl (20.9 g, 0.139 mol) and the reaction mixture was stirred for 4 h. The solvents were removed in vacuo. EtOAc (300 mL) was added and the solution was washed with sat'd aq NH4Cl (2×100 mL), sat'd aq NaHCO3 (100 mL) and brine (100 mL), dried, filtered and evaporated to give tert-butyl (R)-1-(methoxycarbonyl)-2-(t-butyldimethylsilyloxy)ethylcarbamate (40 g, yield 95%) as an oil that was used without further purification. 1H NMR (CDCl3, 400 MHZ): δ=0.02 (s, 6 H), 0.86 (s, 9 H), 1.45 (s, 9 H), 3.73 (s, 3 H), 3.82 (dd, J=14, 4.4 Hz, 1 H), 4.05 (dd, J=13.2, 3.6 Hz, 1H), 4.35 (m, 1 H), 5.34 (brs, 1 H).

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. additionEtOAc (300 mL) was added
  3. washthe solution was washed with sat'd aq NH4Cl (2×100 mL)
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-91b134c948f94e14b2404335984d2317
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

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