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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline benzylester

HRID 485572
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 485572
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=O)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:22]([O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][CH2:34][CH2:33][NH:32]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH2:22]([O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:15](=[O:17])[C@@H:14]1[CH2:18][CH2:19][CH2:20][N:13]1[C:11](=[O:12])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2733413Proline benzyl ester hydrochlorideHCID 11902919Boc-ala-pro-OH

Produkt 1

HCID 13389836N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline benzylesterAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

N-t-butyloxycarbonyl-L-alanyl-L-proline (4.3 g, 15 m mole), L-proline benzyl ester hydrochloride (3.7 g, 15.3 m mole) and HOBt (2.0 g, 15 m mole) were dissolved in methylene dichloride (40 ml). WSC (2.8 ml) was added dropwise to the above mixture while cooling to -15° C. and stirring. The reaction was carried out for 3 hours at a temperature of not more than 0° C., and then overnight at room temperature. The solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate, and washed with 1N hydrochloric acid, water, 5% sodium bicarbonate and water, in order. The mixture was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was crystallized with a mixture of ethyl acetate and n-hexan to give a crystal of N-t-butyloxycarbonyl-L-alanyl-L-prolyl-L-proline benzyl ester (6.3 g, 88.7%) having melting point of 143° to 145° C. and specific rotatory power of [α]D25 =-131.0° (C=1, chloroform).

Aufarbeitung

  1. customovernight
  2. customat room temperature
  3. customThe solvent was removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N hydrochloric acid, water, 5% sodium bicarbonate and water, in order
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was crystallized with a mixture of ethyl acetate and n-hexan

Quellen und Nachweise

ORD-Eintrag
ord-7f5c582b04404c12a8cbda1ba3587ad8
Quelldatensatz
uspto-grants-1985_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04536395

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