Benzenamine, 4-(4-morpholinyl)- → 5-(S)-Acetamidomethyl-3-[4'-(4''-morpholinophenylamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

HRID 1861227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861227
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20]C3C(F)=C(F)C(F)=C(F)C=3F)=O)=[C:14]([F:32])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[O:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=2)[CH2:35][CH2:34]1>N1C=CC=CC=1.CN(C)C=O>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([NH:43][C:42]3[CH:41]=[CH:40][C:39]([N:36]4[CH2:37][CH2:38][O:33][CH2:34][CH2:35]4)=[CH:45][CH:44]=3)=[O:20])=[C:14]([F:32])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 229661965-(S)-acetamidomethyl-3-[4'-(pentafluorophenoxy)carbonyl-3'-fluorophenyl]oxazolidine-2-one

Produkt 1

HCID 206583735-(S)-Acetamidomethyl-3-[4'-(4''-morpholinophenylamino)carbonyl-3'-fluorophenyl]-oxazolidine-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

BAL resin immobilized 5-(S)-acetamidomethyl-3-[4′-(pentafluorophenyl)oxycarbonyl-3′-fluorophenyl]oxazolidine-2-one (0.100g, 0.029 mmol) was agitated with 4-morpholinoaniline (0.155 mg, 0.87 mmol) in 10% pyridine in dimethylformamide (2 ml) for 24 h. The resin was filtered and washed liberally with dimethylformamide, MeOH, DCM, and dried under vacuum. The dry resin was cleaved in 60% trifluoroacetic acid in dichloromethane (2 ml) for 2 h at room temperature. The supernatant was evaporated under vacuum, and the crude product was purified by preparative TLC (eluent: 10% methanol in dichloromethane to give product as a white solid. Yield 6.6 mg (50%). MS (m/z): 457.2 [M+H]+. 1H NMR.

Aufarbeitung

  1. filtrationThe resin was filtered
  2. washwashed liberally with dimethylformamide, MeOH, DCM
  3. customdried under vacuum
  4. customThe supernatant was evaporated under vacuum
  5. customthe crude product was purified by preparative TLC (eluent
  6. custom10% methanol in dichloromethane to give product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-df39db6e1c884e088cbc0fe1187de1b3
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531470B1

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