Tetrabutylammonium Fluoride → [5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanol

HRID 1882090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882090
[Si]([O:18][CH2:19][C:20]1[S:21][C:22]([C:25]2[NH:26][C:27]([CH:30]([C:38]3[CH:43]=[CH:42][C:41]([S:44]([CH:47]4[CH2:49][CH2:48]4)(=[O:46])=[O:45])=[CH:40][CH:39]=3)[CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:28][CH:29]=2)=[N:23][N:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:47]1([S:44]([C:41]2[CH:42]=[CH:43][C:38]([CH:30]([C:27]3[NH:26][C:25]([C:22]4[S:21][C:20]([CH2:19][OH:18])=[N:24][N:23]=4)=[CH:29][CH:28]=3)[CH2:31][CH:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)=[CH:39][CH:40]=2)(=[O:45])=[O:46])[CH2:49][CH2:48]1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 1361666602-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole

Produkt 1

HCID 136166657[5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl]methanolAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3,4-thiadiazole (122 mg) in tetrahydrofuran (1.2 mL) was added tetrabutylammonium fluoride (0.44 mL: 1M tetrahydrofuran solution), and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (51.3 mg, yield 63%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio). melting point 208.5-208.6° C. MS: 474 (MH+).

Aufarbeitung

  1. washwashed with saturated brine
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-81eada0ea6e04b2fb2dcdca15668ef4f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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