4-Bromophenol → trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide

HRID 2360319ノート

反応式

HRID 2360319 の反応式
CS([O:5][C@H:6]1[C@H:10]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:9][O:8][CH2:7]1)(=O)=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>C(#N)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:5][C@@H:6]2[CH2:7][O:8][CH2:9][C@H:10]2[NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 86653047HCID 86653047、化合物

生成物 1

HCID 67194484trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

In a microwave vial, a solution of trans-4-[(isopropylsulfonyl)amino]tetrahydrofuran-3-yl methanesulfonate (546 mg, 1.90 mmol) in acetonitrile (8 mL) was combined with 4-bromophenol (97%, 407 mg, 2.28 mmol) and cesium carbonate (929 mg, 2.85 mmol). The reaction was irradiated in a microwave reactor at 160° C. for 2 hours, then cooled to room temperature and treated with saturated aqueous sodium bicarbonate solution (10 mL). The reaction was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Gradient: 20% to 50% ethyl acetate in heptane), to afford trans-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide. Yield: 626 mg, 1.72 mmol, 91%. LCMS m/z 361.9 (M−1). 1H NMR (400 MHz, CDCl3) δ 1.38 (d, J=6.9 Hz, 3H), 1.40 (d, J=6.8 Hz, 3H), 3.19 (septet, J=6.8 Hz, 1H), 3.82 (br d, J=8.0, 1H), 3.91 (dd, J=10.6, 1.7 Hz, 1H), 4.02-4.08 (m, 2H), 4.24 (dd, J=10.5, 4.7 Hz, 1H), 4.85 (br d, J=4.7 Hz, 1H), 4.95 (br d, J=8.3 Hz, 1H), 6.88 (d, J=9.0 Hz, 2H), 7.40 (d, J=9.0 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ 16.45, 16.71, 54.14, 58.70, 71.45, 71.81, 82.07, 113.97, 117.20, 132.52, 155.75.

後処理

  1. customThe reaction was irradiated in a microwave reactor at 160° C. for 2 hours
  2. extractionThe reaction was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (Gradient: 20% to 50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-7782dbbdb9ec4ab4bec4666b9d5beb56
出典データセット
uspto-grants-2014_04
特許番号
US08686043B2

反応ノート

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