Sodium hydride → {9-[(Phenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester

HRID 51320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51320
[H-].[Na+].[C:3]1([CH2:9][N:10]2[C:22]3[CH:21]=[C:20]([CH3:23])[CH:19]=[C:18]([OH:24])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][C:15]=3[C:25](=[O:27])[NH2:26])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C.C1COCC1.C(OCC)(=O)C>[C:3]1([CH2:9][N:10]2[C:22]3[CH:21]=[C:20]([CH3:23])[CH:19]=[C:18]([O:24][CH2:29][C:30]([O:32][CH3:33])=[O:31])[C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][C:15]=3[C:25](=[O:27])[NH2:26])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 227393719-[(Phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole

Produkt 1

HCID 21304100{9-[(Phenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

60% Sodium hydride in mineral oil (30.4 mg, 0.76 mM) was added to a solution of 9-[(phenyl)methyl]-2-methyl-4-hydroxy-5-carbamoyl carbazole (202 mg, 0.61 mM) in 21 mL DMF and 4.6 ml THF. After 10 minutes, methyl bromoacetate (77 μl, 0.482 mM) was added and the resultant mixture stirred at room temperature for 1.25 hours. The mixture was diluted with ethyl acetate and washed with H2O. The aqueous layer was extracted with ethyl acetate. The combined organic layers were extracted with saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (elution with ethyl acetate) to afford 184 mg (75%) of {9-[(phenyl)methyl]-2-methyl-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester. 1H NMR (DMSO-d6) δ7.55 (d, 1H, J=8 Hz), 7.5 (bs, 1H), 7.4-7.15 (m, 9H), 6.45 (s, 1H), 5.7 (s, 2H), 4.9 (s, 2H), 3.75 (s, 3H), 2.4 (s, 3H). MS (FD) m/e 386, 403.

Aufarbeitung

  1. washwashed with H2O
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined organic layers were extracted with saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (elution with ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bbfccb42ccf44f36906f23892f8daaf7
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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