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 1825309Notes

Reaction equation

HRID 1825309 reaction equation
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]

Participants

6

Reactant 2

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

Product 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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-8fdb53df80534507a5dc20e3893821f5
Source dataset
uspto-grants-2006_05
Patent number
US07045658B2

Reaction notes

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