Triethylamine → Nepsilon-Benzyloxycarbonyl-Nalpha-(tert-butoxycarbonyl)-L-lysyl-L-phenylalanyl-L-leucine ethyl ester

HRID 477712

Reaktionsgleichung

Reaktionsgleichung von HRID 477712
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:29])[C@H:12]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH2:16])[CH3:9].C(N(CC)CC)C.[CH2:37]([O:44][C:45]([NH:47][CH2:48][CH2:49][CH2:50][CH2:51][C@@H:52]([C:61](O)=[O:62])[NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])=[O:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[CH2:8]([O:10][C:11](=[O:29])[C@H:12]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:13][C:14](=[O:24])[C@H:15]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:16][C:61](=[O:62])[C@H:52]([CH2:51][CH2:50][CH2:49][CH2:48][NH:47][C:45]([O:44][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:46])[NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:58])[CH3:59])=[O:55])[CH3:9]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2724765Boc-Lys(Z)-OHHCID 67716275HCID 67716275, Verbindung

Produkt 1

HCID 15021173Nepsilon-Benzyloxycarbonyl-Nalpha-(tert-butoxycarbonyl)-L-lysyl-L-phenylalanyl-L-leucine ethyl esterAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a mixture of 1.68 g (4 mmol) of L-phenylalanyl-L-leucine ethyl ester trifluoroacetate, 0.56 mL (4 mmol) of triethylamine and 32 mL of chloroform were added at 0° C., first 1.52 g (4 mmol) of Nε -benzyloxycarbonyl-Nα -(tert-butoxycarbonyl)-L-lysine, and the 0.83 g (4 mmol) of dicyclohexylcarbodiimide, each being added in a single portion. The reaction mixture was warmed gradually to room temperature and then stirred overnight at that temperature. The precipitate which formed was removed by filtration. The filtrate was evaporated in vacuo and the residue was chromatographed on silica gel using 3:1 methylene chloride/ethyl acetate as eluent to give 2.48 g (92.7%) of the title compound as a white solid melting at 135°-136° C. after crystallization from a mixture of ethyl acetate and isopropyl ether. The product has the structural formula: ##STR110## as further confirmed by NMR, IR and elemental analyses.

Aufarbeitung

  1. additionwere added at 0° C.
  2. customThe precipitate which formed
  3. customwas removed by filtration
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel using 3:1 methylene chloride/ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-62af76f7c30f4512a7db392dd7d10549
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888427

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