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

HRID 2230406Notes

Reaction equation

HRID 2230406 reaction equation
C(OC([NH:11][C@H:12]([C:17]([NH:19][C@@H:20]([CH2:49][OH:50])[C@@H:21]([OH:48])[C@@H:22]([OH:47])[C@H:23]([OH:46])[C:24]([NH:26][C@H:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:28][C:29]([O:31][CH2:32][O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=O)C1C=CC=CC=1>CO.[Pd]>[OH:46][C@@H:23]([C@H:22]([OH:47])[C@H:21]([OH:48])[C@@H:20]([NH:19][C:17](=[O:18])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH2:11])[CH2:49][OH:50])[C:24]([NH:26][C@H:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:28][C:29]([O:31][CH2:32][O:33][C:34](=[O:39])[C:35]([CH3:36])([CH3:37])[CH3:38])=[O:30])=[O:25]

Participants

4

Reactant 1

HCID 53899016pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate

Product 1

HCID 59902696pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionateYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionate (150 mg) in methanol (5 ml) was added 10% palladium on activated carbon (30 mg) and the mixture was stirred under hydrogen atmosphere at room temperature for 1.5 hours. After removal of the catalyst by filtration, the filtrate was concentrated under reduced pressure. Recrystallization from ethyl acetate-hexane provided the title compound (101 mg).

Workup

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

Sources & evidence

ORD record
ord-f5a57a547ddc477f81e2908cd3af265c
Source dataset
uspto-grants-2002_07
Patent number
US06423869B1

Reaction notes

Loading…