Ethyl Acetate → N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 2-[(N,N-diethyl)amino]ethyl ester

HRID 844894

Reaktionsgleichung

Reaktionsgleichung von HRID 844894
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([NH:11][C@H:12]([C:31]([OH:33])=[O:32])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:16][CH:15]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].C(O[CH2:44][CH3:45])(=O)C>O>[CH2:9]([N:11]([CH2:44][CH2:45][O:32][C:31](=[O:33])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21](=[O:30])[N:22]([CH3:29])[C:23](=[O:28])[N:24]([CH3:27])[C:25]=2[CH3:26])=[CH:18][CH:19]=1)[NH:11][C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[O:10])[CH2:12][CH3:13])[CH3:3]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69337579CH9Z955RV6

Produkt 1

HCID 18736695N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 2-[(N,N-diethyl)amino]ethyl esterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylaianine (1.0 mmol, 460 mg), 2-[(N,N-diethyl)aminolethyl chloride hydrochloride (8.05 mmol, 1.43 g) and potassium carbonate (8.05 mmol, 1.11 g) in ethyl acetate (5 mL) and water (5 mL) was stirred at room termperature overnight. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×40 mL). The combined extracts were washed with brine (50 mL) and dried over anhydrous sodium sulfate. Filtration of the drying agent and concentration of the filtrate gave the crude product which was purified by silica gel chromatography using a Biotage (40m) column to obtain 426 mg (76% yield) of N-[(2,6-difluorophenyl)carbonyl]-4-(1,3,6-trimethyl-2,4-dioxo-5-pyrimidinyl)-L-phenylalanine 2-[(N,N-diethyl)amino]ethyl ester as an amorphous white solid. ES-HRMS m/e calcd for C29H34F2N4O5 (M+H) 557.2570, found 557.2575.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×40 mL)
  3. washThe combined extracts were washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationFiltration of the drying agent and concentration of the filtrate
  6. customgave the crude product which
  7. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-55b88d1e9450478b9a20d182d49697d0
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380387B1

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