6-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate → 3-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dione

HRID 857096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857096
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[C:27](=[O:28])[CH2:26][NH:25][C:24]2=[O:29])[CH:18]=1)(=O)=O.[NH2:30][CH2:31][C@@H:32]([C:34]1[CH:45]=[CH:44][C:37]2[O:38][C:39]([CH3:43])([CH3:42])[O:40][CH2:41][C:36]=2[CH:35]=1)[OH:33]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:42][C:39]1([CH3:43])[O:38][C:37]2[CH:44]=[CH:45][C:34]([C@@H:32]([OH:33])[CH2:31][NH:30][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]([N:23]4[C:27](=[O:28])[CH2:26][NH:25][C:24]4=[O:29])[CH:20]=[CH:21][CH:22]=3)=[CH:35][C:36]=2[CH2:41][O:40]1

Komponenten

5

Edukt 2

HCID 218672176-{4-[3-(2,5-Dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonateHCID 56600231(1R)-2-Amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-YL)ethanol

Produkt 1

HCID 693439983-(3-{4-[(6-{[(2R)-2-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}hexyl)oxy]butyl}phenyl)imidazolidine-2,4-dioneAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 6-{4-[3-(2,5-dioxoimidazolidin-1-yl)phenyl]butoxy}hexyl methanesulfonate (766 mg) in DMF (8 ml) was treated with tetrabutylammonium bromide (578 mg) and (1R)-2-amino-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (544 mg) and the mixture was stirred at 20° C. for 3 d. The solvent was removed under reduced pressure, the residue was dissolved in CH2Cl2, washed with water and purified by chromatography on Biotage (40 g) eluting with 3% 2M NH3 in MeOH:CH2Cl2 to give the title compound (417 mg). ES+ve 554 (MH)+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. custompurified by chromatography on Biotage (40 g)
  5. washeluting with 3% 2M NH3 in MeOH

Quellen und Nachweise

ORD-Eintrag
ord-fa08fb941b7f408493cdbe8dc12f1042
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144908B2

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