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

HRID 1675272노트

반응식

HRID 1675272 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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 (1 H, d, J=1.6 Hz), 7.81 (2 H, d, J=8.2 Hz), 7.69 (2 H, d, J=8.2 Hz), 7.04-7.23 (5 H, m), 6.95 (1 H, d, J=7.8 Hz), 6.79 (2 H, d, J=9.0 Hz), 6.15 (1 H, d, J=1.6 Hz), 4.91 (2 H, s), 4.44 (1 H, t, J=7.8 Hz), 3.08 (1H, dd, J=16.4, 8.2 Hz), 2.83 (1 H, dd, J=16.4, 7.4 Hz). 6.28 Example 33

후처리

  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

출처 및 근거

ORD 기록
ord-0406adc923d44deebcaab8ddd4d91665
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003648B2

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