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

HRID 430802

Reaktionsgleichung

Reaktionsgleichung von HRID 430802
[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].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:61]([NH2:65])([CH3:64])([CH3:63])[CH3:62]>CN(C=O)C.CCOCC>[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:65][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:27])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 6385Tert-ButylamineHCID 81531DiisopropylethylamineHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

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 2

HCID 3283Diethyl EtherLösungsmittelHCID 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 i-Pr2NEt (1.5 mL, Aldrich, Milwaukee, Wis.) followed by O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium 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, Aldrich, Milwaukee, Wis.). The reaction mixture was stirred for 1 hour at 0° C. and warmed to room temperature. The reaction mixture was then poured into Et2O, and washed sequentially with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution. The organic phase was dried over 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. washwashed sequentially with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by chromatography (silica gel, 3:1 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ffb257c994604a6284a9c938c8f41e60
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323243B1

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