Triethylamine → N-[(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionyl]-L-alanine

HRID 2230414

Reaktionsgleichung

Reaktionsgleichung von HRID 2230414
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](O)=[O:30])=[O:25])=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])=O)C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O:61][C:62](=[O:66])[C@H:63]([CH3:65])[NH2:64])C1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>C(#N)C.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]([CH3:16])[CH3:15])[NH2:11])[CH2:41][OH:42])[C:24]([NH:26][C@H:27]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:28][C:29]([NH:64][C@H:63]([C:62]([OH:66])=[O:61])[CH3:65])=[O:30])=[O:25]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2802424L-Alanine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)HCID 59902690(S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid

Produkt 1

HCID 59902665N-[(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionyl]-L-alanineAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To absolution of (S)-3-[(2S,3R,4R,5S)-5-(N-benzyloxycarbonyl-L-leucyl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid (200 mg), L alanine benzyl ester p-toluenesulfonate (238 mg) and N-hydroxy-5-norbornene-2,3-dicarboxyimide (183 mg) in acetonitrile (10 ml) were added N,N′-dicyclohexylcarbodimide (140 mg) and triethylamine (0.094 ml) and the mixture was stirred at room temperature for 15 hours. The formed insoluble solid was filtrated off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated brine, followed by drying over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was dissolved in methanol (10 ml) and stirred at room temperature with 10% palladium on activated carbon (60 mg) under hydrogen atmosphere for 3 hours. After filtration, the filtrate was concentrated under reduced pressure to give a residue, which was passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to afford the title compound (58 mg).

Aufarbeitung

  1. filtrationThe formed insoluble solid was filtrated off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialby drying over anhydrous sodium sulfate
  6. customRemoval of the organic solvent
  7. customgave a residue, which
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto give a residue, which
  11. washfollowed by elution with water-acetonitrile
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was recrystallized from methanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-81b0012bb3eb419cb1cb87ceef6c4d08
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06423869B1

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