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

HRID 1675272ノート

反応式

HRID 1675272 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-0406adc923d44deebcaab8ddd4d91665
出典データセット
uspto-grants-2011_08
特許番号
US08003648B2

反応ノート

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