Triphenylphosphine → N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-{4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl}hex-5-enamide

HRID 2104929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2104929
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:10](=[O:19])[CH:9]2[CH2:20][CH2:21][CH:22]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:4][CH:3]=1.[CH3:38][N:39]([CH2:47][CH:48]([OH:57])[CH:49]([OH:56])[CH:50]([OH:55])[CH:51]([OH:54])[CH2:52][OH:53])[C:40](=[O:46])[CH2:41][CH2:42][CH2:43][CH:44]=[CH2:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][N:39]([CH2:47][CH:48]([OH:57])[CH:49]([OH:56])[CH:50]([OH:55])[CH:51]([OH:54])[CH2:52][OH:53])[C:40](=[O:46])[CH2:41][CH2:42][CH2:43][CH:44]=[CH:45][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:9]([CH2:20][CH2:21][CH:22]([O:30][Si:31]([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:32])[CH3:33])[C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[C:10](=[O:19])[N:11]2[C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 11776TriphenylphosphineHCID 22252040N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)hex-5-enamideHCID 222520774-(4-Bromophenyl)-3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)azetidin-2-one

Produkt 1

HCID 68552127N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)-6-{4-[3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenyl}hex-5-enamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

110 mg of 4-(4-bromophenyl)-3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)azetidin-2-one and 136 mg of N-methyl-N-(2,3,4,5,6-pentahydroxyhexyl)hex-5-enamide are initially charged in 300 μl of triethylamine under argon in a closed tube which had been heated thoroughly beforehand. After addition of 6 mg of palladium acetate and 14 mg of triphenylphosphine, the mixture is stirred at 100° C. for 4 h. The reaction mixture is then taken up in dichloromethane, filtered and concentrated using a rotary evaporator. Purification of the residue using an SiO2 cartridge (dichloromethane/methanol 20:1-5:1) gives the product. C43H58F2N2O8Si (796)

Aufarbeitung

  1. temperaturehad been heated thoroughly
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. customPurification of the residue
  6. customgives the product

Quellen und Nachweise

ORD-Eintrag
ord-a6dc06cbecc646bab4d0e1c4d83fa059
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576200B2

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