Sulfur → HCID 88214287, Verbindung

HRID 2269307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269307
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[C:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:20][CH:19]=1)[O:16][CH3:17].[S]>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@@H:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:20][CH:19]=1)[O:16][CH3:17]

Komponenten

4

Edukt 2

HCID 5362487SulfurHCID 88215764HCID 88215764, Verbindung

Produkt 1

HCID 88214287HCID 88214287, VerbindungAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound of Example 17 (640 mg, 1.5 mmol) was dissolved in THF (50 mL) and hydrogenated in the presence of sulfur-resistant 10% palladium on carbon (640 mg) on a Parr Shaker at 50 PSI for 20 hours. The catalyst was removed via filtration through diatomaceous earth and the filtrate was concentrated in vacuo. The residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1) plus 5% acetic acid, to afford crude material which was further purified by (dissolving the residue in 50 mL of ethyl acetate, washing with water (25 mL), saturated aqueous sodium bicarbonate (25 mL), brine (25 mL) and drying (MgSO4), to afford a colorless gum (229 mg, 35%). 1HNMR (300 MHz, CDCl3): δ2.0 (m, 2H), 2.3 (s, 3H), 2.5 (t, 2H), 3.1 (dd, 1H), 3.2 (s, 3H), 3.5 (dd, 1H), 4.1 (dd, 1H), 4.4 (dd, 1H), 7.2 (m, 4H), 7.4 (m, 3H), 7.9 (m, 2H), 8.1 (bs, 1H, NH).

Aufarbeitung

  1. customThe catalyst was removed via filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified on silica gel
  4. washeluting with hexane/ethyl acetate (3/1) plus 5% acetic acid
  5. customto afford crude material which
  6. customwas further purified by (
  7. dissolutiondissolving the residue in 50 mL of ethyl acetate
  8. washwashing with water (25 mL), saturated aqueous sodium bicarbonate (25 mL), brine (25 mL)
  9. dry with materialdrying (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-4b3b75f3c0404fc49bec5eeccbd7c3e1
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329408B1

Notizen zur Reaktion

Wird geladen…