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Sulfuric acid magnesium salt (1:1) → 4-(2-{2-[(2R)-2-methyl-5-oxo-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile

HRID 1064771
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HRID 1064771 반응식
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:14][C:12]=2[CH:13]=1.[O-:26][Mn](=O)(=O)=O.[K+].[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O.O>[CH3:1][C@@H:2]1[CH2:6][CH2:5][C:4](=[O:26])[N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)=[CH:14][C:12]=2[CH:13]=1
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참가 물질

6

반응물 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 9818903Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-

생성물 1

HCID 675340094-(2-{2-[(2R)-2-methyl-5-oxo-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile수율 2%

시약·촉매·용매 2

HCID 180Acetone
용매
HCID 962Water용매

실험 절차

The mono-(L)-tartaric acid salt of the product of Example 1D (96 mg, 0.20 mmol) was suspended in acetone (10 mL) and treated with a solution of KMnO4 (158 mg, 1.0 mmol) and MgSO4 (120 mg, 1.0 mmol) in water (5 mL) over 30 minutes. After the purple color had disappeared, the solids were filtered off. The filtrate was diluted with EtOAc, washed with aqueous potassium dihydrogen phosphate, concentrated, and purified by HPLC [Waters Nova-Pak HR C18 column (25 mm×100 mm, 6 μm particle size) using a gradient of 10% to 100% MeCN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min.] to provide the title compound (2% yield). MS (ESI APCI) m/z 345 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.22 (d, 3 H), 1.55-1.64 (m, 1 H), 2.15-2.32 (m, 2 H), 2.34-2.42 (m, 1 H), 2.99-3.13 (m, 2 H), 3.39-3.46 (m, 1 H), 3.68-3.76 (m, 1 H), 3.89-3.97 (m, 1 H), 6.65 (s, 1 H), 7.51-7.56 (m, 2 H), 7.76-7.84 (m, 5 H).

후처리

  1. filtrationthe solids were filtered off
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with aqueous potassium dihydrogen phosphate
  4. concentrationconcentrated
  5. custompurified by HPLC [Waters Nova-Pak HR C18 column (25 mm×100 mm, 6 μm particle size)
  6. customover 8 min
  7. custom(10 min run time)

출처 및 근거

ORD 기록
ord-fe607b999c1d4fff8a75e0165848223b
출처 데이터셋
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06969730B2

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