Tert-Butylamine → (S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester

HRID 278878

Reaktionsgleichung

Reaktionsgleichung von HRID 278878
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([OH:27])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14](OCC2C=CC=CC=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]([NH2:32])([CH3:31])([CH3:30])[CH3:29]>CN(C=O)C>[CH3:4][C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:25]([NH:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:27])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 6385Tert-ButylamineHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

Produkt 1

HCID 11809380(S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl esterAusbeute 153,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of N-(tert-butyloxycarbonyl)-O-benzyl-L-tyrosine (Bachem, 2.00 g, 5.38 mmol) in 20 mL of DMF was cooled to 0° C. and treated with iPr NEt (1.5 mL) followed by O-benzotriazol-1-yl-N,N,N′,N′-bis(tetramethylene)-uronium hexafluoro phosphate (2.04 g, 5.38 mmol, Novabiochem, La Jolla, Calif.). The resulting suspension was stirred for 30 minutes at 0° C. and then treated with tert-butylamine (0.48 g, 6.56 mmol). The reaction mixture was stirred for 1 hour at 0° C. and warmed to room temperature. The reaction mixture was poured into Et O and washed sequentially with saturated aqueous NaHCO3 solution, and saturated aqueous NaCl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate) to give (S)-[2-[(1,1-dimethylethyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-carbamic acid 1,1-dimethylethyl ester (2.65 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 1 hour at 0° C.
  2. temperaturewarmed to room temperature
  3. additionThe reaction mixture was poured into Et O
  4. washwashed sequentially with saturated aqueous NaHCO3 solution, and saturated aqueous NaCl solution
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-962f5357127445a9b30f7e2e42ca3032
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362174B1

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