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

HRID 2235612Notes

Reaction equation

HRID 2235612 reaction equation
C([C@H]1COC(=O)N1C(=O)[CH2:15][C@@H:16]([C:22]1[CH:49]=[CH:48][C:25]([O:26][CH2:27][C:28]2[CH:29]=[C:30]([NH:34][S:35]([C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=3)(=[O:37])=[O:36])[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:51]O.[Li+].[OH-].Cl.C1[CH2:60][O:59]CC1>O>[F:46][C:44]([F:45])([F:47])[C:41]1[CH:40]=[CH:39][C:38]([S: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:48]=[CH:49][C:22]([C@@H:16]([C:17]3[CH:21]=[CH:20][O:19][N:18]=3)[CH2:15][C:60]([OH:59])=[O:51])=[CH:23][CH:24]=2)(=[O:37])=[O:36])=[CH:43][CH:42]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59300604N-(3-((4-((S)-3-((S)-4-Benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenyl)-4-(trifluoromethyl)-benzenesulfonamide

Product 1

HCID 24898550(S)-3-(4-(3-(4-Trifluoromethylphenylsulfonamido)benzyloxy)-phenyl)-3-(isoxazol-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the oxazolidinone (32.1) (17.0 mg, 0.0241 mmol) dissolved in THF (2 mL), was added a 30% hydrogen peroxide solution (27.0 μL, 0.241 mmol) followed by a 2 M LiOH solution (60.0 μL, 0.121 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 32 (6.00 mg). MS ESI (pos.) m/e: 547.0 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.32 (1H, d, J=1.6 Hz), 7.81 (2H, d, J=8.2 Hz), 7.69 (2H, d, J=8.2 Hz), 7.04-7.23 (5H, m), 6.95 (1H, d, J=7.8 Hz), 6.79 (2H, d, J=9.0 Hz), 6.15 (1H, d, J=1.6 Hz), 4.91 (2H, s), 4.44 (1H, t, J=7.8 Hz), 3.08 (1H, dd, J=16.4, 8.2 Hz), 2.83 (1H, dd, J=16.4, 7.4 Hz).

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-68b2eba97a1a485688def84d5b4405bd
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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