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 2230406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2230406
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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 59902696pivaloyloxymethyl (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionateAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f5a57a547ddc477f81e2908cd3af265c
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423869B1

Notizen zur Reaktion

Wird geladen…