1-(4-Methylbenzenesulfonyl)aziridine → [3-(4-Chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propyl]-4-methyl-benzenesulfonamide

HRID 564342

反応式

HRID 564342 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[C:17]([F:18])=[C:16]([F:19])[CH:15]=[CH:14][C:13]=2[F:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Li][CH2:22][CH2:23][CH2:24][CH3:25].[C:26]1(C)[CH:31]=C[C:29]([S:32]([N:35]2CC2)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C1COCC1.CN(CCN(C)C)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:12]2[C:13]([F:20])=[CH:14][CH:15]=[C:16]([F:19])[C:17]=2[F:18])[CH2:25][CH2:24][C:23]2[CH:22]=[C:26]([CH3:31])[CH:27]=[CH:28][C:29]=2[S:32]([NH2:35])(=[O:34])=[O:33])(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 5612741-(4-Methylbenzenesulfonyl)aziridineHCID 589503342-(4-Chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzeneHCID 178418339Butyllithium

生成物 1

HCID 131729296[3-(4-Chloro-benzenesulfonyl)-3-(2,3,6-trifluoro-phenyl)-propyl]-4-methyl-benzenesulfonamide収率 54.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 86588997Thf tmeda溶媒

実験手順

A solution of 2-(4-chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene (5.6 g, 17.5 mmol) in THF/TMEDA (5:1, 180 mL) at −78° C. was treated with n-BuLi (12 mL, 17.5 mmol, 1.5 M in hexanes). After 15 min, a solution of N-p-toluenesulfonyl aziridine (3.5 g, 17.5 mmol, prepared as described in Eur. J. Org. Chem. 2002, 3004) in THF (10 mL) was added, and the reaction mixture warmed slowly to ambient temperature. After 4 h, the reaction mixture was quenched with 1N HCl and extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (25→50% EtOAc/Hex) provided the title compound (4.9 g, 54%): 1H NMR (CDCl3 400 MHz) δ 7.64 (d, J=8.1 Hz, 2H), 7.57 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.1 Hz, 2H), 7.28 (d, J=8.1 Hz, 2H), 7.14 (m, 1H), 6.75 (m, 1H), 4.81 (m, 1H), 3.17 (ddd, J=7.1, 7.1, 5.6 Hz, 1H), 2.96 (m, 1H), 2.64 (m, 1H), 2.47 (m, 1H), 2.41 (s, 3H).

後処理

  1. waitAfter 4 h
  2. customthe reaction mixture was quenched with 1N HCl
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-631d4db9398848089264d4ee1eeb1764
出典データセット
uspto-grants-2011_11
特許番号
US08067621B2

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