N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide → N1-(4-hydroxybutyl)-N3-{(1S)-2-hydroxy-1-(4-hydroxybenzyl)-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N1-propylisophthalamide

HRID 348839Notes

Reaction equation

HRID 348839 reaction equation
C([O:8][C:9]1[CH:57]=[CH:56][C:12]([CH2:13][C@H:14]([NH:28][C:29](=[O:55])[C:30]2[CH:53]=[C:52]([CH3:54])[CH:51]=[C:32]([C:33]([N:35]([CH2:39][CH2:40][CH2:41][CH2:42][O:43]CC3C=CC=CC=3)[CH2:36][CH2:37][CH3:38])=[O:34])[CH:31]=2)[C@H:15]([OH:27])[CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[OH:43][CH2:42][CH2:41][CH2:40][CH2:39][N:35]([CH2:36][CH2:37][CH3:38])[C:33](=[O:34])[C:32]1[CH:51]=[C:52]([CH3:54])[CH:53]=[C:30]([C:29]([NH:28][C@@H:14]([CH2:13][C:12]2[CH:56]=[CH:57][C:9]([OH:8])=[CH:10][CH:11]=2)[CH:15]([OH:27])[CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)=[O:55])[CH:31]=1

Participants

4

Reactant 1

HCID 68609530N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide

Product 1

HCID 68608790N1-(4-hydroxybutyl)-N3-{(1S)-2-hydroxy-1-(4-hydroxybenzyl)-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N1-propylisophthalamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N1-{(1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3—-[4-(benzyloxy)butyl]-5-methyl-N3-propylisophthalamide (X, 100 mg, 0.130 mmol) and palladium on carbon (10%, 100 mg) in absolute glacial acetic acid (5 mL) is shaken under an atmosphere of hydrogen at 35 psi for 5 hours. The resulting mixture is filtered through diatomaceous earth and washed with methanol. The combined filtrates are concentrated under reduced pressure. The concentrate is purified by flash column chromatography (silica; gradent of dichloromethane/methanol/ammonium hydroxide 97/3/0.05 to 93/7/0.05) to give the title compound: NMR (300 MHz, CD3OD): δ 7.55–6.64, 4.19, 3.99–3.72, 3.63–3.36, 3.21–3.09, 2.79–2.69, 2.39, 1.90–1.40, 1.29 and 1.02–0.6; ESI-MS (m/z) [M+H]+=592.

Workup

  1. filtrationThe resulting mixture is filtered through diatomaceous earth
  2. washwashed with methanol
  3. concentrationThe combined filtrates are concentrated under reduced pressure
  4. customThe concentrate is purified by flash column chromatography (silica; gradent of dichloromethane/methanol/ammonium hydroxide 97/3/0.05 to 93/7/0.05)

Sources & evidence

ORD record
ord-d9a9c94f696246aab4bd161dd77ca6c3
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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