Water → tert-butyl{[5-(3-cyano-2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 2090757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2090757
[F:1][C:2]1[C:7]([CH:8]=[N:9]O)=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]1[N:15]([S:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:14]=[C:13]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:12]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.O>O1CCCC1>[C:8]([C:7]1[C:2]([F:1])=[C:3]([C:11]2[N:15]([S:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)(=[O:17])=[O:18])[CH:14]=[C:13]([CH2:25][N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])[CH:12]=2)[CH:4]=[CH:5][CH:6]=1)#[N:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86631005tert-butyl {[5-{2-fluoro-3-[(hydroxyimino)methyl]phenyl}-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Produkt 1

HCID 66974580tert-butyl{[5-(3-cyano-2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamateAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution (5 mL) of tert-butyl {[5-{2-fluoro-3-[(hydroxyimino)methyl]phenyl}-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (150 mg) in tetrahydrofuran were added triethylamine (93 mg) and methanesulfonyl chloride (84 mg) at room temperature. The reaction mixture was stirred at 70° C. for 8 hr, and cooled to room temperature. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1) to give the title compound as a pale-yellow oil (yield 106 mg, 73%).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1)

Quellen und Nachweise

ORD-Eintrag
ord-af4434a6df024f119049f8bf9dbcf1b1
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436187B2

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