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 749248Notes

Reaction equation

HRID 749248 reaction equation
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

Participants

5

Reactant 1

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

Product 1

HCID 693184974-Hydroxy-7-({[6-(4-phenylbutoxy)hexyl]amino}acetyl)-1,3-benzothiazol-2(3H)-oneYield 10.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8afa535283b645298aca1e36c80aa782
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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