(S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionamide → (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionamide

HRID 2230408Notes

Reaction equation

HRID 2230408 reaction equation
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:41][OH:42])[C@@H:21]([OH:40])[C@@H:22]([OH:39])[C@H:23]([OH:38])[C:24]([NH:26][C@H:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:28][C:29]([NH2:31])=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=O)C1C=CC=CC=1>CO.[Pd]>[OH:38][C@@H:23]([C@H:22]([OH:39])[C@H:21]([OH:40])[C@@H:20]([NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH2:11])[CH2:41][OH:42])[C:24]([NH:26][C@H:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:28][C:29]([NH2:31])=[O:30])=[O:25]

Participants

4

Reactant 1

HCID 59902676(S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionamide

Product 1

HCID 59902691(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionamideYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionamide (200 mg) in methanol (10 ml) was added 10% palladium on activated carbon (50 mg) and the mixture was stirred under hydrogen atmosphere at room temperature for 20 hours. After removal of the catalyst by filtration, the filtrate was concentrated under reduced pressure. Recrystallization from methanol-diethylether provided the title compound (140 mg).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customRecrystallization from methanol-diethylether

Sources & evidence

ORD record
ord-3b76c71dc55e48ae9ae148210a418b5b
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

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