HCID 69818250, compound → HCID 69818475, compound

HRID 2417422Notes

Reaction equation

HRID 2417422 reaction equation
C([N:8]([C@H:20]([CH2:34][OH:35])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][CH2:32][CH3:33])=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:32]([NH:31][C:29]([NH:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][C@H:20]([NH:8][CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:34][OH:35])=[CH:27][CH:26]=1)=[O:30])[CH3:33]

Participants

4

Reactant 1

HCID 69818250HCID 69818250, compound

Product 1

HCID 69818475HCID 69818475, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]-N′-ethylurea (73 mg) in methanol (1.5 ml) was hydrogenated (1 atm) over 10% palladium on carbon (11 mg) at room temperature for 12 hours. After the catalyst was filtered off, the filtrate was concentrated and the residue was purified by column chromatography (silica gel, chloroform/methanol) followed by recrystallization from ehtanol/hexane to give N-ethyl-N′-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]-propyl]phenyl]urea (38 mg) as a white powder.

Workup

  1. customat room temperature
  2. customfor 12 hours
  3. filtrationAfter the catalyst was filtered off
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by column chromatography (silica gel, chloroform/methanol)
  6. customfollowed by recrystallization from ehtanol/hexane

Sources & evidence

ORD record
ord-f1aac32679234d3f9e962dbd6cba462a
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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