4-(4-(2-[((2S)-3-(4-(Benzyloxy)-3-[(methylsulfonyl)amino]phenoxy)-2-hydroxypropyl)amino]ethyl}anilino)-N-octyl-1-piperidinecarboxamide → 4-(4-[2-[(2s)-2-Hydroxy-3-(4-hydroxy-3-methanesulfonylamino-phenoxy)-propylamino]-ethyl]-phenylamino)-piperidine-1-carboxylic acidoctylamide

HRID 396042Notes

Reaction equation

HRID 396042 reaction equation
C([O:8][C:9]1[CH:46]=[CH:45][C:12]([O:13][CH2:14][C@@H:15]([OH:44])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:43]=[CH:42][C:23]([NH:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:32])[CH2:27][CH2:26]3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:47][S:48]([CH3:51])(=[O:50])=[O:49])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH2:34]([NH:33][C:31]([N:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:23]2[CH:22]=[CH:21][C:20]([CH2:19][CH2:18][NH:17][CH2:16][C@H:15]([OH:44])[CH2:14][O:13][C:12]3[CH:45]=[CH:46][C:9]([OH:8])=[C:10]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:11]=3)=[CH:43][CH:42]=2)[CH2:26][CH2:27]1)=[O:32])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 2

HCID 699874684-(4-(2-[((2S)-3-(4-(Benzyloxy)-3-[(methylsulfonyl)amino]phenoxy)-2-hydroxypropyl)amino]ethyl}anilino)-N-octyl-1-piperidinecarboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 101682414-(4-[2-[(2s)-2-Hydroxy-3-(4-hydroxy-3-methanesulfonylamino-phenoxy)-propylamino]-ethyl]-phenylamino)-piperidine-1-carboxylic acidoctylamideYield 38.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(4-(2-[((2S)-3-(4-(Benzyloxy)-3-[(methylsulfonyl)amino]phenoxy)-2-hydroxypropyl)amino]ethyl}anilino)-N-octyl-1-piperidinecarboxamide (0.15 g, 0.207 mmol) was dissolved in ethanol (70 mL) and 10% palladium on carbon (0.043 g) added. The solution was shaken in a Parr apparatus at 50 psi hydrogen atmosphere for 16 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: 10:1 going to 5:1 chloroform-methanol containing 2% triethylamine) to give the title compound (0.052 g, 0.08 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: 10:1 going to 5:1 chloroform-methanol containing 2% triethylamine)

Sources & evidence

ORD record
ord-aa20afcff61f4a8a893d71e1370c6ebf
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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