Dicyclohexylcarbodiimide → N-(1-Carboxyethyl)-L-alanyl-L-proline

HRID 1758837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758837
C(C(N[C@H](C(O)=O)C)C)(OCC1C=CC=CC=1)=O.Cl.C(OC(=O)[C@@H]1CCCN1)C1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:50]([CH:60]([NH:62][C@H:63]([C:65]([N:67]1[CH2:74][CH2:73][CH2:72][C@H:68]1[C:69]([OH:71])=[O:70])=[O:66])[CH3:64])[CH3:61])([O:52]CC1C=CC=CC=1)=[O:51]>N1C=CC=CC=1.C(N(CC)CC)C>[C:50]([CH:60]([NH:62][C@H:63]([C:65]([N:67]1[CH2:74][CH2:73][CH2:72][C@H:68]1[C:69]([OH:71])=[O:70])=[O:66])[CH3:64])[CH3:61])([OH:52])=[O:51]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 2733413Proline benzyl ester hydrochlorideHCID 54011285HCID 54011285, VerbindungHCID 54407250HCID 54407250, Verbindung

Produkt 1

HCID 53882949N-(1-Carboxyethyl)-L-alanyl-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Dissolve 0.75 g of N-(1-carbobenzoxyethyl)-L-alanine in pyridine and add 7.5 ml of 1 M triethylamine in pyridine. Cool, and add 1.09 g L-proline benzyl ester hydrochloride and 0.678 g dicyclohexylcarbodiimide. Store at 0° C. for 20 hours. Filter, then concentrate the reaction mixture in vacuo. Dissolve the residue in ethyl acetate and wash this solution with saturated K2CO3, then brine. Dry the organic phase, concentrate in vacuo, then chromatograph the residue on silica gel with ethyl acetate-hexane to isolate the diastereoisomeric mixture of N-(1-carbobenzoxyethyl)-L-alanyl-L-proline.

Aufarbeitung

  1. temperatureCool
  2. filtrationFilter
  3. concentrationconcentrate the reaction mixture in vacuo
  4. dissolutionDissolve the residue in ethyl acetate
  5. washwash this solution with saturated K2CO3
  6. customDry the organic phase
  7. concentrationconcentrate in vacuo
  8. customchromatograph the residue on silica gel with ethyl acetate-hexane to isolate

Quellen und Nachweise

ORD-Eintrag
ord-82f6eee09e4f489f9c5ad9d8d6f68716
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374829

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