Tetrabutylammonium Fluoride → HCID 68842200, Verbindung

HRID 660793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660793
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N:24]1[CH2:28][C:27](=[O:29])[N:26](CC[Si](C)(C)C)[S:25]1(=[O:37])=[O:36])[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N:24]1[CH2:28][C:27](=[O:29])[NH:26][S:25]1(=[O:37])=[O:36])[CH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 68842500HCID 68842500, Verbindung

Produkt 1

HCID 68842200HCID 68842200, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzyl}-benzonitrile (57 mg, 0.107 mmol) in THF (10 mL) is added TBAF (0.16 mL, 1.5 equiv) and the mixture is stirred at 60° C. for 2 h. The mixture is partitioned between EtOAc and 1N HCl. The organic phase is washed with 1N HCl and brine then is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 0-40% EtOAc/hexane as eluent to give the title compound.

Aufarbeitung

  1. customThe mixture is partitioned between EtOAc and 1N HCl
  2. washThe organic phase is washed with 1N HCl and brine
  3. dry with materialthen is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fcfc05eb1ea84ef9b8df4d719f7cb5bc
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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