7-({Benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one → 4-Hydroxy-7-({[6-(4-phenylbutoxy)hexyl]amino}acetyl)-1,3-benzothiazol-2(3H)-one

HRID 749248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749248
C([N:8]([CH2:26][C:27]([C:29]1[C:37]2[S:36][C:35](=[O:38])[NH:34][C:33]=2[C:32]([OH:39])=[CH:31][CH:30]=1)=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C1C=CC=CC=1>C(O)C.C(O)(=O)C.[Pd]>[OH:39][C:32]1[C:33]2[NH:34][C:35](=[O:38])[S:36][C:37]=2[C:29]([C:27](=[O:28])[CH2:26][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]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:30][CH:31]=1

Komponenten

5

Edukt 1

HCID 693185017-({Benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one

Produkt 1

HCID 693184974-Hydroxy-7-({[6-(4-phenylbutoxy)hexyl]amino}acetyl)-1,3-benzothiazol-2(3H)-oneAusbeute 10,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 7-({benzyl[6-(4-phenylbutoxy)hexyl]amino}acetyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one (100 mg) in dry ethanol (10 ml) and acetic acid (0.5 ml) was added to 10% Pd/C catalyst (40 mg) and stirred under hydrogen for 20 h. The catalyst was collected by filtration through celite and the filtrate evaporated in vacuo. The residue was purified on SCX and then silica SPE cartridge, eluting with a stepped gradient of 1-10% methanol-dichloromethane mixtures, to give the title compound (9 mg). LCMS RT=2.81 min.

Aufarbeitung

  1. filtrationThe catalyst was collected by filtration through celite
  2. customthe filtrate evaporated in vacuo
  3. customThe residue was purified on SCX
  4. washsilica SPE cartridge, eluting with a stepped gradient of 1-10% methanol-dichloromethane mixtures

Quellen und Nachweise

ORD-Eintrag
ord-8afa535283b645298aca1e36c80aa782
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402598B2

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