4-phenyl-2,3-dihydro-1H-imidazol-2-one → (4S)-5,5-dimethyl-3-(4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)phenyl)-4-phenyl-1,3-oxazolidin-2-one

HRID 525390Notes

Reaction equation

HRID 525390 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]([CH3:20])([CH3:19])[O:10][C:9]2=[O:21])=[CH:4][CH:3]=1.[C:22]1([C:28]2[NH:29][C:30](=[O:33])[NH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH3:19][C:11]1([CH3:20])[O:10][C:9](=[O:21])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([N:31]3[CH:32]=[C:28]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:29][C:30]3=[O:33])=[CH:3][CH:4]=2)[C@H:12]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 110626774-phenyl-2,3-dihydro-1H-imidazol-2-oneHCID 89813884(S)-3-(4-iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Product 1

HCID 89815381(4S)-5,5-dimethyl-3-(4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)phenyl)-4-phenyl-1,3-oxazolidin-2-oneYield 9%

Procedure

The title compound was prepared as described in General Scheme B using intermediate C in place of intermediate B and 4-phenyl-1H-imidazol-2(3H)-one (commercially available from Sigma-Aldrich, Milwaukee, Wis.). Purification was performed using preparative LC/MS with 0.1% NH4OH in ACN and water as the mobile phase. The pure fractions were dried under reduced pressure to afford (4S)-5,5-dimethyl-3-(4-(2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)phenyl)-4-phenyl-1,3-oxazolidin-2-one as a white solid (15 mg, 0.055 mmol, 9% yield). 1H NMR (400 MHz, DMSO-d6) δ=11.01 (br. s., 1H), 7.71-7.65 (m, 2H), 7.62-7.50 (m, 4H), 7.41-7.34 (m, 4H), 7.34-7.20 (m, 4H), 5.49 (s, 1H), 1.65 (s, 3H), 0.92 (s, 3H). m/z (ESI) 426.2 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customPurification
  3. customThe pure fractions were dried under reduced pressure

Sources & evidence

ORD record
ord-9008ea770f7a422f929921142975d229
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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