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

HRID 1979275Notes

Reaction equation

HRID 1979275 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

BAL resin immobilized 5-(S)-acetamidomethyl-3-[4′-(pentafluorophenyl)oxycarbonyl-3′-fluorophenyl]oxazolidine-2-one (0.100 g, 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.

Workup

  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

Sources & evidence

ORD record
ord-cfb379e836084f4c86be773baa4a91f2
Source dataset
uspto-grants-2001_05
Patent number
US06239152B1

Reaction notes

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