1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → dibenzylphosphoryl-L-alanyl-L-prolyl-D-proline benzylester

HRID 485579

Reaktionsgleichung

Reaktionsgleichung von HRID 485579
[CH2:1]([P:8]([NH:17][C@H:18]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24](O)=[O:25])=[O:21])[CH3:19])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:41]([O:48][C:49](=[O:55])[C@H:50]1[CH2:54][CH2:53][CH2:52][NH:51]1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:41]([O:48][C:49](=[O:55])[C@H:50]1[CH2:54][CH2:53][CH2:52][N:51]1[C:24](=[O:25])[C@@H:23]1[CH2:27][CH2:28][CH2:29][N:22]1[C:20](=[O:21])[C@H:18]([CH3:19])[NH:17][P:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochlorideHCID 53804723Dibenzylphosphory-L-alanyl-L-proline

Produkt 1

HCID 70042657dibenzylphosphoryl-L-alanyl-L-prolyl-D-proline benzylester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

Dibenzylphosphoryl-L-alanyl-L-proline (1.4 g, 3.2 m mole), HOBt (476 mg, 3.5 m mole) and oily D-proline benzylester hydrochloride (968 mg, 4 m mole) were dissolved in DMF (5 ml) and WSC (0.64 ml, 3.5 m mole) were added thereto while cooling to -15° C. The reaction was carried out for 3 hours under cooling and then overnight at room temperature, and ethyl acetate (100 ml) was added to the reaction solution. The mixture was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order, and then dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain an oily dibenzylphosphoryl-L-alanyl-L-prolyl-D-proline benzylester.

Aufarbeitung

  1. temperatureunder cooling
  2. washThe mixture was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4278354626a442569975784828bff59f
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536395

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