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

HRID 564342

반응식

HRID 564342 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 86588997Thf tmeda용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-631d4db9398848089264d4ee1eeb1764
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067621B2

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