Water → 3-(((1S)-2-Hydroxy-1-methylethyl)oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-(4-(methylsulfonyl)phenoxy)benzamide

HRID 20497

Reaktionsgleichung

Reaktionsgleichung von HRID 20497
C[Si](I)(C)C.C[O:7][CH2:8][C@H:9]([CH3:37])[O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15].O>C(#N)C>[OH:7][CH2:8][C@H:9]([CH3:37])[O:10][C:11]1[CH:12]=[C:13]([CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:34])=[O:35])=[CH:29][CH:28]=2)[CH:25]=1)[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH3:22])[N:18]=1)=[O:15]

Komponenten

5

Edukt 3

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 116195273-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide

Produkt 1

HCID 115251163-(((1S)-2-Hydroxy-1-methylethyl)oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-(4-(methylsulfonyl)phenoxy)benzamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Trimethylsilyl iodide (11.1 mL, 76.3 mmol) was added to a solution of 3-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide (7.00 g, 15.3 mmol) in dry acetonitrile (100 mL) under argon for 21 h. Water (40 mL) was added to quench the reaction and the acetonitrile was removed in vacuo. The residue was diluted with ethyl acetate-(200 mL) and 1M aqueous hydrochloric acid. The organic layer was separated and further washed with 10% w/v aqueous sodium thiosulfate pentahydrate to remove residual iodine. The organic layer Was separated, dried (MgSO4), filtered and evaporated and purified by column chromatography, eluting with 3% to 5% methanol in DCM, to give the title compound as a white foam (5.70 g, 84%). Recrystallisation from hot ethanol (125 mg/mL) afforded the title compound as colourless needles (87% recovery). Mpt 126-132° C.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. customthe acetonitrile was removed in vacuo
  4. additionThe residue was diluted with ethyl acetate-(200 mL) and 1M aqueous hydrochloric acid
  5. customThe organic layer was separated
  6. washfurther washed with 10% w/v aqueous sodium thiosulfate pentahydrate
  7. customto remove residual iodine
  8. customThe organic layer Was separated
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. custompurified by column chromatography
  13. washeluting with 3% to 5% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-22fd2514f4c84eba8a59504b3fabf9ec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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