Dicyclohexylcarbodiimide → Boc-(D)Ala-Gly-OBzl

HRID 467354

Reaktionsgleichung

Reaktionsgleichung von HRID 467354
[NH2:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[NH:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:14]([C:16](O)=[O:17])[CH3:15].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C>[NH:13]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C@@H:14]([C:16]([NH:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:17])[CH3:15]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 409140Benzyl glycinateHCID 637606BOC-D-alanine

Produkt 1

HCID 15567200Boc-(D)Ala-Gly-OBzl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 7.4 g H-Gly-OBzl.p-Tos-OH, 100 ml acetonitrile was added, and this was followed by cooling with ice, then 3.1 ml TEA, 3.78 g Boc-D-Ala-OH, 3.96 g HONB and 4.54 g DCC were added, and this was followed by agitation for one night. The resulting DCU was filtered, and the filtrate was concentrated, then the resulting residue was dissolved in 300 ml AcOEt. The resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citrate, after which it was dried with Na2SO4. The dried product, after concentration, was crystallized with petroleum benzine and collected by filtration.

Aufarbeitung

  1. temperatureby cooling with ice
  2. waitthis was followed by agitation for one night
  3. filtrationThe resulting DCU was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionthe resulting residue was dissolved in 300 ml AcOEt
  6. washThe resulting solution was washed with 4% aqueous NaHCO3 and 10% aqueous citrate
  7. dry with materialafter which it was dried with Na2SO4
  8. concentrationThe dried product, after concentration
  9. customwas crystallized with petroleum benzine
  10. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-19479433fbc3461c879e4c0ae89705b2
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05159061

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