Ethyl Acetate → HCID 178510469, Verbindung

HRID 1873596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873596
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH:13]([O:16][CH2:17][CH2:18][O:19][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:40][C:41]2[N:42]=[C:43]([C:46]3[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][CH:47]=3)[S:44][CH:45]=2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C@H:10]2[CH2:15][CH2:14][C@@H:13]([O:16][CH2:17][CH2:18][OH:19])[CH2:12][CH2:11]2)[C:5]([C:37]#[N:38])=[C:4]([S:39][CH2:40][C:41]2[N:42]=[C:43]([C:46]3[CH:47]=[CH:48][C:49]([Cl:52])=[CH:50][CH:51]=3)[S:44][CH:45]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68699977HCID 68699977, Verbindung

Produkt 1

HCID 178510469HCID 178510469, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

43 mg (0.06 mmol) of the compound from Example 7A (cis isomer) are dissolved in 5 ml of dry THF, 22 mg (0.08 mmol) of tetra-n-butylammonium fluoride are added and the mixture is stirred at RT for 20 h. 15 ml of ethyl acetate are then added to the mixture. The mixture is washed twice with in each case 3 ml of saturated aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the crude product is purified chromatographically initially by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5) and then once more on silica gel 60 (mobile phase: gradient dichloromethane/ethanol 200:1→10:1).

Aufarbeitung

  1. washThe mixture is washed twice with in each case 3 ml of saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customAfter removal of the solvent
  4. customon a rotary evaporator the crude product
  5. customis purified chromatographically initially by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-b3162cfc6b4e40b1a16e3f26374a1824
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304412B2

Notizen zur Reaktion

Wird geladen…