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

HRID 400523

反応式

HRID 400523 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-928c3c5599504ecb958c80d785b26cae
出典データセット
uspto-grants-2014_06
特許番号
US08741899B2

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