4-(4-{2-[(2R)-2-(4-Benzyloxy-3-methanesulfonylamino-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamide → 4-(4-{2-[(2r)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acidoctylamide

HRID 396037Notes

Reaction equation

HRID 396037 reaction equation
[CH2:1]([NH:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C@@H:29]([C:31]3[CH:36]=[CH:35][C:34]([O:37]CC4C=CC=CC=4)=[C:33]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:32]=3)[OH:30])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[H][H]>C(O)C.[Pd]>[CH2:1]([NH:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][NH:27][CH2:28][C@H:29]([OH:30])[C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:32]=3)=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 233813424-(4-{2-[(2R)-2-(4-Benzyloxy-3-methanesulfonylamino-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 101889984-(4-{2-[(2r)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acidoctylamideYield 62.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-{2-[(2R)-2-(4-Benzyloxy-3-methanesulfonylamino-phenyl)-2-hydroxy-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylicacid octylamide (0.152 g, 0.219 mmol) was dissolved in ethanol (40 mL) and 10% palladium on carbon (0.05 g) added. The solution was shaken in a Parr apparatus at 50 psi hydrogen atmosphere for 2 hours, filtered through a Celite pad and the solvent removed in vacuo. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 5:1 chloroform-methanol) to furnish the title compound (0.082 g, 0.136 mmol)

Workup

  1. filtrationfiltered through a Celite pad
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by flash chromatography on silica gel Merck-60 (eluant: 5:1 chloroform-methanol)

Sources & evidence

ORD record
ord-d515bc36913d47178bc0079915aaa1fd
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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