Dimethylformamide → tert-Butyl [(1S)-2-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate

HRID 724726노트

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HRID 724726 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:11]2[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1I.[C:38]([N:42]1[C:46](=[O:47])[CH:45]=[CH:44][S:43]1(=[O:49])=[O:48])([CH3:41])([CH3:40])[CH3:39].C(N(CC)CC)C.CN(C)C=O>CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[C:11]2[N:12]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[C:44]1[S:43](=[O:48])(=[O:49])[N:42]([C:38]([CH3:40])([CH3:39])[CH3:41])[C:46](=[O:47])[CH:45]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 111168162-Tert-butyl-2,3-dihydro-1lambda6,2-thiazole-1,1,3-trioneHCID 58746876tert-Butyl [(1S)-2-(3-bromo-4-iodophenyl)-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate

생성물 1

HCID 58746634tert-Butyl [(1S)-2-[3-bromo-4-(2-tert-butyl-1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate수율 24%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매

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온도
70 °C

실험 절차

A solution of tert-butyl [(1S)-2-(3-bromo-4-iodophenyl)-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate (130 mg, 112 μmol), 2-tert-butylisothiazol-3(2H)-one 1,1-dioxide (42.3 mg, 223 μmol), triethylamine (46.7 mL, 335 μmol), palladium acetate (25.1 mg, 112 μmol), N,N-dimethylformamide (3.0 mL) and tetra-N-butylammonium chloride (31.0 mg, 112 μmol) was degassed and stirred at 70° C. for 2 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (20.0 mg, 24%). MF=C35H47BrN4O6SSi; LCMS found for C35H48BrN4O6SSi (M+H)+: m/z=759.

후처리

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-99929a71af1c46a59075e03f2864b502
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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