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 1825309ノート

反応式

HRID 1825309 の反応式
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]

参加物

6

反応物 2

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

生成物 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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-8fdb53df80534507a5dc20e3893821f5
出典データセット
uspto-grants-2006_05
特許番号
US07045658B2

反応ノート

読み込み中…