Fumaric Acid → (E)-but-2-enedioic acid;N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[6-[4-(3-sulfamoylphenyl)butoxy]hexylamino]ethyl]phenyl]formamide

HRID 1825309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825309
C([N:8]([CH2:30][C@@H:31]([C:33]1[CH:38]=[CH:37][C:36]([O:39]CC2C=CC=CC=2)=[C:35]([NH:47][CH:48]=[O:49])[CH:34]=1)[OH:32])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][C:18]#[C:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)C1C=CC=CC=1.[C:50]([OH:57])(=[O:56])/[CH:51]=[CH:52]/[C:53]([OH:55])=[O:54]>C(O)C.[Pd].[OH-].[OH-].[Pd+2]>[C:50]([OH:57])(=[O:56])/[CH:51]=[CH:52]/[C:53]([OH:55])=[O:54].[CH:48]([NH:47][C:35]1[CH:34]=[C:33]([C@@H:31]([OH:32])[CH2:30][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=2)[CH:38]=[CH:37][C:36]=1[OH:39])=[O:49]

Komponenten

6

Edukt 2

HCID 444972Fumaric AcidHCID 426256683-(4-{[6-(benzyl{(2R)-2-[4-(benzyloxy)-3-(formylamino)phenyl]-2-hydroxyethyl}amino)hexyl]oxy}but-1-ynyl)benzenesulfonamide

Produkt 1

HCID 44572221(E)-but-2-enedioic acid;N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[6-[4-(3-sulfamoylphenyl)butoxy]hexylamino]ethyl]phenyl]formamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-(4-{[6-(benzyl{(2R)-2-[4-(benzyloxy)-3-(formylamino)phenyl]-2-hydroxyethyl}amino)hexyl]oxy}but-1-ynyl)benzenesulfonamide (320 mg) in ethanol (15 ml) was hydrogenated in the presence of 10% palladium on carbon (50 mg) and palladium hydroxide on carbon (100 mg) at 100 p.s.i for 18 h. The catalyst was filtered off onto celite and the filtrate was evaporated to dryness. The residual oil was purified by chromatography on Biotage (8 g) cartridge eluting with dichloromethane/ethanol/0.88 ammonia (25:8:1). The residual oil (118 mg) was dissolved in methanol (20 ml) and treated with fumaric acid (0.5 equivalent) and evaporated to give the title compound (80 mg). LCMS RT=2.39 min, ES+ve 508 (MH)+.

Aufarbeitung

  1. filtrationThe catalyst was filtered off onto celite
  2. customthe filtrate was evaporated to dryness
  3. customThe residual oil was purified by chromatography on Biotage (8 g) cartridge
  4. washeluting with dichloromethane/ethanol/0.88 ammonia (25:8:1)
  5. dissolutionThe residual oil (118 mg) was dissolved in methanol (20 ml)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8fdb53df80534507a5dc20e3893821f5
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045658B2

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