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 1825309노트

반응식

HRID 1825309 반응식
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]

참가 물질

6

반응물 2

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

생성물 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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-8fdb53df80534507a5dc20e3893821f5
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045658B2

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