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

HRID 1783261Notes

Reaction equation

HRID 1783261 reaction equation
C([O:8][C:9]1[CH:48]=[CH:47][C:12]([CH2:13][C@H:14]([NH:28][C:29](=[O:46])[C:30]2[CH:44]=[C:43]([CH3:45])[CH:42]=[C:32]([C:33]([N:35]([CH2:39][CH2:40][CH3:41])[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:27][C@H:15]([CH2:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=1)[C@@H:14]([NH:28][C:29](=[O:46])[C:30]1[CH:44]=[C:43]([CH3:45])[CH:42]=[C:32]([C:33]([N:35]([CH2:36][CH2:37][CH3:38])[CH2:39][CH2:40][CH3:41])=[O:34])[CH:31]=1)[CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:48][CH:47]=1

Participants

4

Reactant 1

HCID 68609943N1-((1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N3,N3-dipropylisophthalamide

Product 1

HCID 68611527N1-{(1S,2R)-2-hydroxy-1-(4-hydroxybenzyl)-3-[(3-methoxybenzyl)amino]propyl}-5-methyl-N3,N3-dipropylisopthalamide

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}-5-methyl-N3,N3-dipropylisophthalamide (140 mg, 0.215 mmol) and palladium on carbon (10%, 140 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; methylene chloride/methanol/ammonium hydroxide gradient from 97/3/0.05 to 93/7/0.05) to give the title compound, IR (KEBr) 2962, 2931, 1611, 1594 and 1263 cm−1, ESI-MS (m/z) [M+H]+=562.

Workup

  1. filtrationis 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; methylene chloride/methanol/ammonium hydroxide gradient from 97/3/0.05 to 93/7/0.05)

Sources & evidence

ORD record
ord-49c78949a2c04ac882f087cc3b012b59
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Reaction notes

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