Hydrochloric Acid → (S)-3-(4-(3-(4-(Trifluoromethyl)benzamido)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

HRID 1675262Notes

Reaction equation

HRID 1675262 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:49])[CH2:15][C@@H:16]([C:22]1[CH:48]=[CH:47][C:25]([O:26][CH2:27][C:28]2[CH:29]=[C:30]([NH:34][C:35](=[O:46])[C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)[CH:31]=[CH:32][CH:33]=2)=[CH:24][CH:23]=1)[C:17]1[CH:21]=[CH:20][O:19][N:18]=1)C1C=CC=CC=1.[OH:50]O.[Li+].[OH-].Cl>C1COCC1.O>[F:44][C:42]([F:43])([F:45])[C:39]1[CH:40]=[CH:41][C:36]([C:35]([NH:34][C:30]2[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=2)[CH2:27][O:26][C:25]2[CH:24]=[CH:23][C:22]([C@@H:16]([C:17]3[CH:21]=[CH:20][O:19][N:18]=3)[CH2:15][C:14]([OH:49])=[O:50])=[CH:48][CH:47]=2)=[O:46])=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 59300570N-(3-((4-((S)-3-((S)-4-Benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenyl)-4-(trifluoromethyl)benzamide

Product 1

HCID 24898325(S)-3-(4-(3-(4-(Trifluoromethyl)benzamido)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acidYield 46.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of oxazolidinone 27.4 (71.8 mg, 0.107 mmol) dissolved in THF (10 mL), was added a 30% hydrogen peroxide solution (0.121 mL, 1.07 mmol) followed by a 2M LiOH solution (0.268 mL, 0.535 mmol). The resulting slurry was stirred for two hours. The reaction mixture was diluted with water and acidified with hydrochloric acid to a pH 3. The mixture was then extracted with EtOAc (1×50 mL), and the organic layer was washed with acidic sodium sulfite solution (2×30 mL), brine (1×30 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC to give 27 (25.2 mg). MS ESI (pos.) m/e 511.1 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.21 (1 H, br. s.), 10.51 (1 H, s), 8.75 (1 H, d, J=1.6 Hz), 8.15 (2 H, d, J=8.2 Hz), 7.91 (2 H, d, J=8.2 Hz), 7.87 (1 H, s), 7.74 (1 H, d, J=8.2 Hz), 7.38 (1 H, t, J=7.8 Hz), 7.23 (2 H, d, J=8.6 Hz), 7.19 (1 H, d, J=7.8 Hz), 6.96 (2 H, d, J=9.0 Hz), 6.50 (1 H, d, J=1.6 Hz), 5.08 (2 H, s), 4.48 (1 H, t, J=7.8 Hz), 3.07 (1 H, dd, J=16.4, 8.2 Hz), 2.88 (1 H, dd, J=16.2, 7.2 Hz).

Workup

  1. extractionThe mixture was then extracted with EtOAc (1×50 mL)
  2. washthe organic layer was washed with acidic sodium sulfite solution (2×30 mL), brine (1×30 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-02754fb0da6a4473815a5bb527ea9106
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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