Hydrochloric Acid → HCID 67331281, compound

HRID 2235638Notes

Reaction equation

HRID 2235638 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:44])[CH2:15][C@H:16]([C:39]1[CH:43]=[CH:42][O:41][N:40]=1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[CH2:26][CH3:27])=[CH:19][CH:18]=1)C1C=CC=CC=1.[OH:45]O.[OH-].[Li+].Cl>C1COCC1.O>[O:41]1[CH:42]=[CH:43][C:39]([C@H:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:36])([F:37])[F:38])=[CH:33][CH:34]=3)[CH2:26][CH3:27])=[CH:21][CH:22]=2)[CH2:15][C:14]([OH:44])=[O:45])=[N:40]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67329823HCID 67329823, compound

Product 1

HCID 67331281HCID 67331281, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the oxazolidinone (49.2) (23.0 mg, 0.038 mmol) dissolved in THF (2 mL), was added a 30% hydrogen peroxide solution (43 μL, 0.38 mmol) followed by a 2 M lithium hydroxide solution (94 μL, 0.19 mmol). The resulting slurry was stirred for one hour. The reaction mixture was then diluted with water and acidified with hydrochloric acid to pH ˜3. The mixture was then extracted with EtOAc (1×20 mL), and the organic layer was washed with an acidic sodium sulfite solution (2×15 mL) and brine (1×15 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC to give 49 (5.5 mg). MS ESI (pos.) m/e: 450.1 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.33 (1H, d, J=1.6 Hz), 7.51 (2H, d, J=8.6 Hz), 7.12 (2H, d), 6.95 (2H, d, J=8.6 Hz), 6.78 (2H, d, J=8.6 Hz), 6.16 (1H, d, J=1.6 Hz), 4.44 (1H, t, J=7.8 Hz), 4.02 (2H, t, J=6.1 Hz), 3.94 (2H, t, J=6.1 Hz), 3.09 (1H, dd, J=16.6, 8.4 Hz), 2.84 (1H, dd, J=16.4, 7.4 Hz), 1.81-1.84 (4H, m).

Workup

  1. extractionThe mixture was then extracted with EtOAc (1×20 mL)
  2. washthe organic layer was washed with an acidic sodium sulfite solution (2×15 mL) and brine (1×15 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-535db1843647463baa77673798ea6c61
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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