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

HRID 240438노트

반응식

HRID 240438 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-806ccaae526a4b27a380eef9af8b93d8
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648074B2

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