Hydrochloric Acid → HCID 131721135, Verbindung

HRID 1417143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417143
[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+].[NH:27]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[C@H:28]([C:33](ON1C(=O)CCC1=O)=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31].Cl>O1CCOCC1.O>[NH:27]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[C@H:28]([C:33]([NH:1][C@H:2]([C:11]([NH:13][C@H:14]([C:19]([OH:21])=[O:20])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11089751N-[(Phenylmethoxy)carbonyl]-L-leucine 2,5-dioxo-1-pyrrolidinyl esterHCID 131721134H-Asp(OtBu)-Leu-OH

Produkt 1

HCID 131721135HCID 131721135, VerbindungAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

The H-Asp(OtBu)-Leu-OH (3.02 g), sodium bicarbonate (1.68 g), and 30 mL of water were mixed to give a mixture of pH 8. Z-Leu-OSu (3.63 g) in dioxane (30 mL) was added to the mixture and was stirred at room temp for 2 h. The reaction mixture was acidified by addition of conc. HCl to pH 1.0, then was extracted with ethyl acetate (30 mL×3). The combined extracts were dried over Na2SO4, filtered, and concentrated. The crude product was dissolved in methanol and chromatographed on a column of Sephadex™ LH20 to yield Z-Leu-Asp(OtBu)-Leu-OH as a foamy solid (4.43 g).

Aufarbeitung

  1. customto give
  2. additiona mixture of pH 8
  3. extractionwas extracted with ethyl acetate (30 mL×3)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude product was dissolved in methanol
  8. customchromatographed on a column of Sephadex™ LH20

Quellen und Nachweise

ORD-Eintrag
ord-7345b48b96344ac08a6f03e84bb02d7a
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05876945

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