HCID 69818591, compound → HCID 69818136, compound

HRID 2417441Notes

Reaction equation

HRID 2417441 reaction equation
C([N:8]([C@H:20]([CH2:41][OH:42])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:40])[C:30]2[CH:39]=[CH:38][C:33]([C:34]([NH:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)=[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]>[OH:42][CH2:41][C@@H:20]([NH:8][CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:40])[C:30]2[CH:39]=[CH:38][C:33]([C:34]([NH:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 1

HCID 69818591HCID 69818591, compound

Product 1

HCID 69818136HCID 69818136, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N1-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]-N4-methylterephthalamide (14.0 mg) in methanol (0.5 ml) was added 10% palladium on activated carbon (50% wet, 14.0 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 to give N1-[4-[(2S)-3-hydroxy-2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]propyl]-phenyl]-N4-methylterephthalamide (9.7 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-21ef1227c4dd429a9ee68f42346dd51a
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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