Morpholine → tert-butoxycarbonyl-(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine

HRID 875152

Reaktionsgleichung

Reaktionsgleichung von HRID 875152
[C:1]([O:5][C:6]([NH:8][C@@:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@:9]([CH3:10])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:11]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 13678038(S)-2-(Boc-amino)-2-phenylpropanoic acid

Produkt 1

HCID 57444165tert-butoxycarbonyl-(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

630 mg (2.374 mmol) of N-(tert-butoxycarbonyl)-2-phenyl-D-alanine were dissolved in 20 mL of dry DMF and O-(benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoborate (TBTU, 1.37 g, 4.27 mmol), morpholine (0.412 mL, 4.73 mmol) and diisopropylethylamine (1.63 mL, 9.5 mol) were added. The mixture was stirred at room temperature for 1 hour, then the solvent was removed and the residue dissolved with dichloromethane. The solution was washed with saturated NaHCO3, brine, water and dried over Na2SO4. 700 mg of the title compound were recovered (88% yield).

Aufarbeitung

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved with dichloromethane
  3. washThe solution was washed with saturated NaHCO3, brine, water
  4. dry with materialdried over Na2SO4
  5. custom700 mg of the title compound were recovered (88% yield)

Quellen und Nachweise

ORD-Eintrag
ord-c2fc58b057564997847ea5cd4f374881
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981089B2

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