Diethyl chlorophosphate → HCID 11350137, Verbindung

HRID 272572

Reaktionsgleichung

Reaktionsgleichung von HRID 272572
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3.[P:21](Cl)([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C>[CH2:24]([O:23][P:21]([NH:1][CH2:2][C:3]1[CH:16]=[CH:15][C:14]2[O:13][C:12]3[C:7]4=[C:8]([C:17](=[O:20])[NH:18][N:19]=[C:6]4[C:5]=2[CH:4]=1)[CH:9]=[CH:10][CH:11]=3)(=[O:22])[O:26][CH2:27][CH3:28])[CH3:25]

Komponenten

4

Edukt 2

HCID 13139Diethyl chlorophosphateHCID 1119635510-(Aminomethyl)[1]benzopyrano[4,3,2-de]phthalazin-3(2H)-one

Produkt 1

HCID 11350137HCID 11350137, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compound 49 (0.5 mmol) in anhydrous DMF (20 mL) was added diethyl chlorophosphate (1.5 mmol). After 3 hours solution was concentrated in vacuo, and 50 mL of water was added. The aqueous layer was extracted with 30 mL of EtOAc twice. Organic layers were combined and washed with 30 mL of brine. Organic layer was dried with MgSO4. Solvent was removed to afford a white solid, which was recrystallized in 10% of EtOAc in hexanes to afford a white solid 54 in 50% yield. MS (ES−): 400; Mp: 222.3-224.5° C.; 1H-NMR (CDCl3, 400 MHz): 10.21 (s, 1H), 8.10 (d, J=2.5 Hz, 1H), 8.03 (d, J=7.5 Hz, 1H), 7.79 (t, J=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.47 (dd, J=8.5 and 2.0 Hz, 1H), 7.22 (d, J=8.5 Hz, 1H), 4.12 (m, 6H), 1.32 (t, J=6.5 Hz, 6H); Anal. Calcd. for C19H20N3O5P.(0.3H2O): C, 56.10; H, 5.10; N, 10.33. Found: C, 56.00; H, 5.03; N, 10.13.

Aufarbeitung

  1. concentrationAfter 3 hours solution was concentrated in vacuo, and 50 mL of water
  2. additionwas added
  3. extractionThe aqueous layer was extracted with 30 mL of EtOAc twice
  4. washwashed with 30 mL of brine
  5. dry with materialOrganic layer was dried with MgSO4
  6. customSolvent was removed
  7. customto afford a white solid, which
  8. customwas recrystallized in 10% of EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-954d85a485854be3b1c49262cb9aed60
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456178B2

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