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

HRID 485578

Reaktionsgleichung

Reaktionsgleichung von HRID 485578
[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.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:51]([O:58][C:59](=[O:63])[C@@H:60]([CH3:62])[NH2:61])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:51]([O:58][C:59](=[O:63])[C@@H:60]([CH3:62])[NH:61][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:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2802425D-Alanine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)HCID 53804723Dibenzylphosphory-L-alanyl-L-proline

Produkt 1

HCID 70040519dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine 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 D-alanine benzylester p-toluene sulfonic acid salt (1.3 g, 3.5 m mole) were dissolved in DMF (5 ml), and WSC (0.64 ml) was added thereto while cooling to -15° C. The reaction was carried out for 3 hours under cooling and then overnight at room temperature. To the reaction solution ethyl acetate (100 ml) was added and the mixture was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order. The mixture was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced, pressure to give oily dibenzylphosphoryl-L-alanyl-L-prolyl-D-alanine benzylester.

Aufarbeitung

  1. temperatureunder cooling
  2. customovernight
  3. customat room temperature
  4. washthe mixture was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order
  5. dry with materialThe mixture was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-952069d4d0804b46addfb15511cafeec
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04536395

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