Water → (7R,8aS)-2-[(3-tert-butyl-4-methoxyphenyl)sulfonyl]-7-[(5-cyclopropyl-pyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine

HRID 240438ノート

反応式

HRID 240438 の反応式
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][NH:17][CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[C:20]([C:24]1[CH:25]=[C:26]([S:32](Cl)(=[O:34])=[O:33])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31])([CH3:23])([CH3:22])[CH3:21].C(N(C(C)C)CC)(C)C.O>ClCCl>[C:20]([C:24]1[CH:25]=[C:26]([S:32]([N:17]2[CH2:16][CH2:15][N:14]3[CH2:19][C@H:11]([O:10][C:7]4[CH:6]=[N:5][C:4]([CH:1]5[CH2:3][CH2:2]5)=[CH:9][N:8]=4)[CH2:12][C@H:13]3[CH2:18]2)(=[O:34])=[O:33])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31])([CH3:23])([CH3:21])[CH3:22]

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 110652633-tert-Butyl-4-methoxy-benzenesulfonyl chlorideHCID 86680449(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine

生成物 1

HCID 71544608(7R,8aS)-2-[(3-tert-butyl-4-methoxyphenyl)sulfonyl]-7-[(5-cyclopropyl-pyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of the product from Example 27B (30 mg, 0.115 mmol) in dichloromethane (1 mL) was added 3-tert-butyl-4-methoxybenzene-1-sulfonyl chloride (36 mg, 0.138 mmol) and diisopropylethylamine (0.040 mL, 0.23 mmol). The resulting mixture was stirred at room temperature for 90 minutes. Water (2 mL) was added, and the mixture was extracted with dichloromethane (2×2 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude product. Purification by column chromatography on silica gel eluting with a solvent gradient of 0-60% ethyl acetate in hexanes gave the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 0.87-1.00 (m, 4H), 1.38 (s, 9H), 1.73-1.87 (m, 1H), 1.91-2.03 (m, 2H), 2.08 (t, J=10.51 Hz, 1H), 2.31 (dd, J=10.17, 5.09 Hz, 1H), 2.37-2.48 (m, 2H), 2.48-2.60 (m, 1H), 2.91-3.05 (m, 1H), 3.63 (dd, J=10.17, 6.78 Hz, 1H), 3.68-3.76 (m, 1H), 3.83-3.90 (m, 1H), 3.90 (s, 3H), 5.23-5.35 (m, 1H), 6.94 (d, J=9.16 Hz, 1H), 7.57-7.66 (m, 2H), 7.91 (d, J=1.36 Hz, 1H), 8.02 (d, J=1.70 Hz, 1H); MS (ESI) m/z 487.1 (M+H)+.

後処理

  1. extractionthe mixture was extracted with dichloromethane (2×2 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude product
  6. customPurification by column chromatography on silica gel eluting with a solvent gradient of 0-60% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-806ccaae526a4b27a380eef9af8b93d8
出典データセット
uspto-grants-2014_02
特許番号
US08648074B2

反応ノート

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