Hydrochloric Acid → (S)-3-(4-(3-Pivalamidobenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

HRID 2235607Notes

Reaction equation

HRID 2235607 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:43])[CH2:15][C@@H:16]([C:22]1[CH:42]=[CH:41][C:25]([O:26][CH2:27][C:28]2[CH:29]=[C:30]([NH:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[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:44]O.[Li+].[OH-].Cl>C1COCC1.O>[C:35]([NH:34][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=1)[CH2:27][O:26][C:25]1[CH:41]=[CH:42][C:22]([C@@H:16]([C:17]2[CH:21]=[CH:20][O:19][N:18]=2)[CH2:15][C:14]([OH:44])=[O:43])=[CH:23][CH:24]=1)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 59252179N-(3-((4-((S)-3-((S)-4-Benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenyl)pivalamide

Product 1

HCID 24898548(S)-3-(4-(3-Pivalamidobenzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acidYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the oxazolidinone 30.1 (62.0 mg, 0.107 mmol) dissolved in THF (10 mL), was added a 30% hydrogen peroxide solution (0.120 mL, 1.07 mmol) followed by a 2M LiOH solution (0.266 mL, 0.533 mmol). The resulting slurry was stirred for five 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) and 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 30 (29.0 mg). MS ESI (pos.) m/e: 423.1 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.32 (1H, d, J=1.6 Hz), 7.92 (1H, br. s.), 7.61 (1H, s), 7.42 (1H, d, J=7.8 Hz), 7.22 (1H, t, J=7.8 Hz), 7.12 (2H, d, J=9.0 Hz), 7.05 (1H, d, J=7.4 Hz), 6.84 (2H, d, J=9.0 Hz), 6.15 (1H, d, J=1.6 Hz), 4.95 (2H, s), 4.43 (1H, t, J=7.8 Hz), 3.08 (1H, dd, J=16.6, 8.4 Hz), 2.83 (1H, dd, J=16.4, 7.4 Hz), 1.16 (9H, s).

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) and 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-a1317fb191544e4f9b82dadd62c66316
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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