HCID 69817657, compound → HCID 69817744, compound

HRID 2417436Notes

Reaction equation

HRID 2417436 reaction equation
C([O:8][C:9]1[CH:40]=[CH:39][C:12]([O:13][CH2:14][C@@H:15]([OH:38])[CH2:16][NH:17][C@H:18]([CH2:36][OH:37])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:28])=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.O1CCOCC1.[Pd]>[OH:37][CH2:36][C@@H:18]([NH:17][CH2:16][C@H:15]([OH:38])[CH2:14][O:13][C:12]1[CH:39]=[CH:40][C:9]([OH:8])=[CH:10][CH:11]=1)[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([NH:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:28])=[CH:24][CH:25]=1

Participants

5

Reactant 1

HCID 69817657HCID 69817657, compound

Product 1

HCID 69817744HCID 69817744, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-[4-[(2S)-2-[[(2S)-3-[4-(Benzyloxy)phenoxy]-2-hydroxypropyl]amino]-3-hydroxypropyl]phenyl]-N′-phenylurea (159 mg) was dissolved in a mixed solvent of methanol (2.5 ml) and 1,4-dioxane (2.5 ml) under heating. After cooling to room temperature, 10% palladium on activated carbon (50% wet, 159 mg) was added and the mixture was hydrogenated at 1 atm for 4 hours. The catalyst was removed by filtration and washed with methanol. The filtrate was concentrated in vacuo to give N-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]propyl]phenyl]-N′-phenylurea (129 mg) as a white solid.

Workup

  1. temperatureunder heating
  2. customThe catalyst was removed by filtration
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-90768cb3e62049fa8bbce19923f48157
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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