HCID 11083343, compound → HCID 11733971, compound

HRID 2230415Notes

Reaction equation

HRID 2230415 reaction equation
C(OC([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:21]([NH:23][C@@H:24]([CH2:58][OH:59])[C@@H:25]([OH:57])[C@@H:26]([OH:56])[C@H:27]([OH:55])[C:28]([NH:30][C@H:31]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH2:32][C:33]([O:35]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:34])=[O:29])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][C:13]([NH:15][C@H:16]([C:21]([NH:23][C@@H:24]([CH2:58][OH:59])[C@@H:25]([OH:57])[C@@H:26]([OH:56])[C@H:27]([OH:55])[C:28]([NH:30][C@H:31]([C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[CH2:32][C:33]([OH:35])=[O:34])=[O:29])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14]

Participants

4

Reactant 1

HCID 11083343HCID 11083343, compound

Product 1

HCID 11733971HCID 11733971, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Diphenylmethyl (S)-3-[(2S,3R,4R,5S)-5-((N-benzyloxycarbonylglycyl)-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (273 ml) was dissolved in methanol (30 ml) and stirred at room temperature with 10% palladium on activated carbon (50 mg) under hydrogen atmosphere for 1.5 hours. After dilution with methanol, the mixture was filtrated and the filtrate was concentrated under reduced pressure to give a residue, which was recrystallized from methanol-diethylether to afford the title compound (154 mg).

Workup

  1. filtrationAfter dilution with methanol, the mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a residue, which
  4. customwas recrystallized from methanol-diethylether

Sources & evidence

ORD record
ord-2ac23a87eab14cd4871450f940bccd3e
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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