Sodium Thiosulfate → HCID 178423543, Verbindung

HRID 1770644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1770644
[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2[CH2:19][C@:18]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH:7]1[CH2:10][S:9][CH2:8]1)=[O:5].C1C=C(Cl)C=C(C(OO)=[O:41])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2[CH2:19][C@:18]([C:24]3[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=3)([C:20]([F:21])([F:22])[F:23])[O:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH:7]1[CH2:8][S+:9]([O-:41])[CH2:10]1)=[O:5]

Komponenten

5

Edukt 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 867270192-methyl-N-(thietan-3-yl)-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide

Produkt 1

HCID 178423543HCID 178423543, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-methyl-N-(thietan-3-yl)-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide in dichloromethane (92 mL) was added m-CPBA (24.3 mmol, 5.58 g) portion wise at 0-5° C., and the reaction mixture was stirred for 10 min. A saturated Na2S2O3 solution was added, and the mixture was stirred for 10 min. The organic layer was washed with sat. NaHCO3 solution, water and brine, dried over MgSO4, filtered and evaporated. Purification over silica gel (eluent: CH2Cl2/EtOAc) yielded the title compound. LCMS (Method GR) 1.13 min, M+ 539/541; 1H NMR (400 MHz, CDCl3) 2.50 (s, 3H), 3.28 (m, 1H), 3.70 (d, 1H), 4.10-4.20 (m, 4H), 4.70 (m, 1H), 6.50 (d, 1H), 7.40-7.70 (1d+4s, 5H), 19F-NMR (CDCl3, 376 MHz): −79.43. Chiral HPLC Method Column: Daicel CHIRALPAK® IB, 3 μm, 0.46 cm×10 cm Mobile phase: Heptan/EtOH 80/20 Retention times of eluting isomers: 4.85 min (8.2%) 5.66 min (91.8%).

Aufarbeitung

  1. stirringthe mixture was stirred for 10 min
  2. washThe organic layer was washed with sat. NaHCO3 solution, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification over silica gel (eluent: CH2Cl2/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0b0f37b3cfa840b0b6affb6e966be600
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09247740B2

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