Potassium Carbonate → HCID 53747773, Verbindung

HRID 257555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257555
[CH3:1][O:2][N:3]=[C:4]([CH2:10][C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:17]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][CH:32]=1)(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:17]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH:10]([C:11](=[O:16])[CH2:12][CH2:13][CH2:14][CH3:15])[C:4](=[N:3][O:2][CH3:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:33][CH:32]=1)(=[O:24])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15282100[2'-(N-t-Butylsulfamoyl)biphenyl-4-yl]methyl bromideHCID 53883597HCID 53883597, Verbindung

Produkt 1

HCID 53747773HCID 53747773, VerbindungAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 50 mg (0.218 mmol) of ethyl 2-methoxyimino-4-oxooctanoate (from Step A), 83 mg (0.218 mmol) of [2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl bromide (from Step E), 36 mg (0.262 mmol) of freshly pulverized anhydrous potassium carbonate, and 0.6 mL of dry DMF was stirred vigorously for 24 hours at room temperature at which time the starting material was all consumed [TLC (5:1 hexane/EtOAc)]. The mixture was partitioned between 10 mL of EtOAc and 10 mL of 0.2N HCl. The EtOAc layer was then washed with 3×10 mL H2O, 1×5 mL brine, and dried briefly over anhydrous sodium sulfate. The filtrate, obtained from filtration over sintered glass, was concentrated to dryness and the resulting residue was flash chromatographed over 20 mL silica gel (column packed using hexane, sample introduced as a solution in CH2Cl2) eluting with 20/1 hexane/ethyl acetate, to give 83 mg (71%) of the desired product as an oil, homogeneous by TLC. Rf =0.35 in 5:1 hexane/EtOAc. 1H NMR (200 MHz, CDCl3, ppm)=δ0.88 (t, J=7.2 Hz, 3H), 1.00 (s, 9H), 1.31 (m, 5H), 1.52 (m, 2H), 2.32 (t, J=7.0 Hz, 2H), 3.03 (m, 1H), 3.40 (m, 1H), 3.61 (s, 1H), 4.04 (s, 3H), 4.25 (m, 3H), 7.16-7.52 (m, 7H), 8.15 (m, 1H), Mass spectrum: FAB (m/e) 531 (M+1)+.

Aufarbeitung

  1. customall consumed [TLC (5:1 hexane/EtOAc)]
  2. customThe mixture was partitioned between 10 mL of EtOAc and 10 mL of 0.2N HCl
  3. washThe EtOAc layer was then washed with 3×10 mL H2O, 1×5 mL brine
  4. dry with materialdried briefly over anhydrous sodium sulfate
  5. customThe filtrate, obtained from filtration over sintered glass
  6. concentrationwas concentrated to dryness
  7. customchromatographed over 20 mL silica gel (column
  8. additionintroduced as a solution in CH2Cl2)
  9. washeluting with 20/1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0e8a3b7b51df4e6f935291b3c0d1b114
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262412

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