Hydrochloric Acid → (S)-3-(4-(3-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

HRID 2235616Notes

Reaction equation

HRID 2235616 reaction equation
C([C@H]1COC(=O)N1C(=O)[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]([C:34]3[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH:35]=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.C1[CH2:59][O:58]CC1>O>[C:43]([O:42][C:40]([N:37]1[CH2:36][CH:35]=[C:34]([C:30]2[CH:29]=[C:28]([CH:33]=[CH:32][CH:31]=2)[CH2:27][O:26][C:25]2[CH:47]=[CH:48][C:22]([C@@H:16]([C:17]3[CH:21]=[CH:20][O:19][N:18]=3)[CH2:15][C:59]([OH:58])=[O:50])=[CH:23][CH:24]=2)[CH2:39][CH2:38]1)=[O:41])([CH3:44])([CH3:46])[CH3:45]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59300696tert-Butyl 4-(3-((4-((S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-(isoxazol-3-yl)-3-oxopropyl)phenoxy)methyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 24898552(S)-3-(4-(3-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the oxazolidinone (34.4) (8.9 mg, 0.013 mmol) dissolved in THF (0.5 mL), was added a 30% hydrogen peroxide solution (15.0 μL, 0.130 mmol) followed by a 2 M LiOH solution (33.0 μL, 0.065 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 (3×10 mL), and the organic layer was washed with an acidic sodium sulfite solution (1×5 mL) and brine (1×5 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure, and the residue was purified by reverse phase HPLC to give 34 (2.60 mg). MS ESI (pos.): m/e 505.1 (M+H). 1H NMR (400 MHz, CD3CN) δ ppm 8.33 (1H, d, J=1.6 Hz), 7.40 (1H, s), 7.20-7.34 (3H, m), 7.13 (2H, d), 6.86 (2H, d, J=9.0 Hz), 6.16 (1H, d, J=1.6 Hz), 6.03 (1H, br. s.), 4.99 (2H, s), 4.44 (1H, t, J=7.8 Hz), 3.90-3.98 (2H, m, J=2.7 Hz), 3.50 (2H, t, J=5.7 Hz), 3.09 (1H, dd, J=16.4, 8.2 Hz), 2.84 (1H, dd, J=16.4, 7.4 Hz), 2.37-2.45 (2H, m, J=2.0 Hz), 1.37 (9H, s).

Workup

  1. extractionThe mixture was then extracted with EtOAc (3×10 mL)
  2. washthe organic layer was washed with an acidic sodium sulfite solution (1×5 mL) and brine (1×5 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-12c0513c0dfc4677b14c105e35d13c2c
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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