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 724726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724726
[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

Komponenten

8

Edukt 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

Produkt 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]carbamateAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-99929a71af1c46a59075e03f2864b502
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141596B2

Notizen zur Reaktion

Wird geladen…