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Potassium Carbonate → HCID 178491256, Verbindung

HRID 1727323
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1727323
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:14][C@H:13](CS([O-])(=O)=O)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]([CH2:23][C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1)=[N+:21]=[N-:22].[F:32][C:33]1[C:34](=[O:40])[NH:35][C:36](=[O:39])[NH:37][CH:38]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>O.CCOC(C)=O.CN(C=O)C>[N:20]([CH2:23][C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1)=[N+:21]=[N-:22].[F:32][C:33]1[C:34](=[O:40])[NH:35][C:36](=[O:39])[N:37]([C@H:13]2[CH2:12][C@@H:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14]2)[CH:38]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 131727295HCID 131727295, VerbindungHCID 178527650HCID 178527650, Verbindung

Produkt 1

HCID 178491256HCID 178491256, VerbindungAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a 50 mL three-neck flask with trans-3-(benzyloxyethyl)cyclobutyl-mesylate (0.34 g, 1.2 mmol), N3-PMB-5-fluoro-uracil (0.36 g, 1.44 mmol), K2CO3 (0.2 g, 1.44 mmol) and 18-crown-6 (0.38 g, 1.44 mmol) inside, dry DMF 10 mL was added under argon to give a light yellow solution with some white solids at the bottom of the flask. After 5 min, start to heat to 120° C. After 24 hr, add 30 mL EtOAc and 20 mL H2O. The organic phase was separated and washed with brine once. The organic phase was dried over MgSO4 and the solvents were evaporated to give the crude product, which was purified by silica gel flash chromatography (Hexane:EtOAc=3:1) to give an off-white solid (0.27 g, 50.9%) combined with some three-membered ring by-products. 1H NMR (CDCl3, 300 MHz): δ 1.72-1.79 (m, 4H), 2.16-2.24 (m, 1H), 2.51-2.60 (m, 2H), 3.43-3.48 (m, 2H), 3.77 (s, 3H), 4.48 (s, 2H), 4.64-4.75 (m, 1H), 5.05 (s, 2H), 6.81-6.84 (d, J=9.0, 2H), 7.29-7.36 (m, 6H), 7.44-7.47 (d, J=9.0, 2H). MS (FAB): expected for C25H27FN2O4 (M+H)+ 439.49. Found 439.20320. IR (neat) νmax 2926, 2854, 1712, 1458, 1377, 1265, 895, 740, 705.

Aufarbeitung

  1. customto give a light yellow solution with some white solids at the bottom of the flask
  2. waitAfter 24 hr
  3. customThe organic phase was separated
  4. washwashed with brine once
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvents were evaporated
  7. customto give the crude product, which
  8. customwas purified by silica gel flash chromatography (Hexane:EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0b244cd8d37a4dac976760796697d087
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495006B2

Notizen zur Reaktion

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