1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Tyr(Bzl)-Pro-OBzl

HRID 256494

Reaktionsgleichung

Reaktionsgleichung von HRID 256494
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([OH:20])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.[NH:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].Cl.CCN=C=NCCCN(C)C>ClCCl>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([N:28]1[CH2:42][CH2:41][CH2:40][C@H:29]1[C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])=[O:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 2733413Proline benzyl ester hydrochloride

Produkt 1

HCID 131715373BOC-Tyr(Bzl)-Pro-OBzlAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A solution of 10.00 g of BOC-Tyr(Bzl)-OH dissolved in 50 ml of dichloromethane was mixed with 6.53 g of H-Pro-OBzl.HCl. To this mixture, under cooling at -5° C., 4.93 ml of WSC was added, followed by stirring at -5° C. for one hour and at room temperature overnight. The reaction mixture was concentrated under reduced pressure, the residue was mixed by shaking with ethyl acetate and 1N hydrochloric acid and separated into liquid layers. The ethyl acetate layer was washed successively twice with 1N hydrochloric acid, twice with saturated aqueous sodium chloride, three times with 5% aqueous sodium hydrogen carbonate and twice with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 14.46 g (yield: 96.1%) of BOC-Tyr(Bzl)-Pro-OBzl as oily product. Rf1 =0.71.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was mixed
  3. stirringby shaking with ethyl acetate and 1N hydrochloric acid
  4. customseparated into liquid layers
  5. washThe ethyl acetate layer was washed successively twice with 1N hydrochloric acid, twice with saturated aqueous sodium chloride, three times with 5% aqueous sodium hydrogen carbonate and twice with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e1afc80ba44c4e7496a5518c27e63786
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04703106

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