Methanol → 4-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]-N-[(1S)-2-hydroxy-1-phenylethyl]benzenesulfonamide

HRID 400523

Reaktionsgleichung

Reaktionsgleichung von HRID 400523
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[CH2:11]1[N:16]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[O:18])[CH2:15][CH2:14][N:13]2[CH2:29][CH2:30][CH2:31][C@H:12]12.C(=O)([O-])[O-].[Na+].[Na+].CO>ClCCl.CN(C)C=O>[CH2:11]1[N:16]([C:17]([C:19]2[CH:20]=[CH:21][C:22]([S:25]([NH:1][C@@H:2]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:3][OH:4])(=[O:27])=[O:26])=[CH:23][CH:24]=2)=[O:18])[CH2:15][CH2:14][N:13]2[CH2:29][CH2:30][CH2:31][C@H:12]12

Komponenten

6

Edukt 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 1347972-Amino-2-phenylethan-1-olHCID 866439254-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonyl chloride

Produkt 1

HCID 468525944-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]-N-[(1S)-2-hydroxy-1-phenylethyl]benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

Then (S)-2-amino-2-phenylethanol (0.494 g, 3.6 mmol) in dichloromethane/N,N-dimethylformamide (5:1, 40 mL) was added to the crude 4-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylcarbonyl]benzenesulfonyl chloride. The mixture was stirred at room temperature for 3 days, then sodium carbonate (0.21 g, 2 mmol) and methanol (10 mL) were added. The mixture was stirred for an additional 30 minutes, then the reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1) to give the titled compound: 1H NMR (500 MHz, DMSO-d6) δ ppm 1.35 (m, 1H), 1.60-2.10 (m, 6H), 2.90-3.20 (m, 4H), 3.30-3.50 (m, 3H), 4.30 (m, 1H), 4.50 (m, 1H), 4.85 (m, 1H), 7.10 (m, 5H), 7.30 (m, 2H), 7.61 (m, 2H), 8.30 (br s, 1H); MS (EST) m/z 430 (M+H)+.

Aufarbeitung

  1. stirringThe mixture was stirred for an additional 30 minutes
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-928c3c5599504ecb958c80d785b26cae
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741899B2

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