Dicyclohexylcarbodiimide → Benzyl L-leucinate

HRID 1418325

Reaktionsgleichung

Reaktionsgleichung von HRID 1418325
[CH3:1][CH:2]([CH2:4][C@@H:5]([NH:9]C(OC(C)(C)C)=O)[C:6]([OH:8])=[O:7])[CH3:3].[CH2:17]1[CH:21]2[CH:22]3C(=O)N(O)C(=O)[CH:23]3[CH:18]1[CH:19]=[CH:20]2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CCOC(C)=O>[NH2:9][C@H:5]([C:6]([O:8][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7])[CH2:4][CH:2]([CH3:1])[CH3:3]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 637604tert-Butoxycarbonyl-D-leucine

Produkt 1

HCID 6451313Benzyl L-leucinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

pTos (21.6 g) was dissolved in DMF (100 ml), and the solution was cooled with ice. TEA (7.7 ml) and Boc-D-Leu-ONB (prepared from Boc-D-Leu--OH. H2O (12.5 g), HONB (9.86 g) and DCC (11.4 g) were added thereto, followed by stirring overnight. The resulting DCU was separated by filtration, and the filtrate was concentrated to obtain a residue. The residue was dissolved in AcOEt, and the resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid. After washing with water, the solution was dried with Na2SO4 and concentrated. Ether was added to the resulting residue to separate out a precipitate, which was collected by filtration.

Aufarbeitung

  1. temperaturethe solution was cooled with ice
  2. additionwere added
  3. customThe resulting DCU was separated by filtration
  4. concentrationthe filtrate was concentrated
  5. customto obtain a residue
  6. washthe resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid
  7. washAfter washing with water
  8. dry with materialthe solution was dried with Na2SO4
  9. concentrationconcentrated
  10. additionEther was added to the resulting residue
  11. customto separate out a precipitate, which
  12. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-8e0604e70dc24857806d6d9ce38d0ab4
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05883075

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