HCID 69818121, compound → HCID 69818040, compound

HRID 2417448Notes

Reaction equation

HRID 2417448 reaction equation
C([N:8]([C@H:28]([CH2:44][OH:45])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:39]2[NH:40][CH:41]=[CH:42][CH:43]=2)=[O:38])=[CH:32][CH:31]=1)[CH2:9][C@H:10]([OH:27])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]CC2C=CC=CC=2)=[CH:15][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[OH:45][CH2:44][C@@H:28]([NH:8][CH2:9][C@H:10]([OH:27])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([NH:36][C:37]([C:39]2[NH:40][CH:41]=[CH:42][CH:43]=2)=[O:38])=[CH:34][CH:35]=1

Participants

4

Reactant 1

HCID 69818121HCID 69818121, compound

Product 1

HCID 69818040HCID 69818040, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[4-[(2S)-2-[N-benzyl-N-[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino]-3-hydroxypropyl]-phenyl]-1H-pyrrole-2-carboxamide (40 mg) in methanol (2.0 ml) was added 10% palladium on activated carbon (50% wet, 10 mg) and the mixture was hydrogenated at 1 atm for 3 hours. The catalyst was filtered off and washed with methanol. The filtrate was concentrated in vacuo and the residue was powdered from ether and dried to give N-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]propyl]-phenyl]-1H-pyrrole-2-carboxamide (26 mg) as a gray powder.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customdried

Sources & evidence

ORD record
ord-969ba5e29a794630bbdeaa57a7022214
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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