Benzyl chloroformate → Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

HRID 1903599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903599
[O:1]=[C:2]1[CH:6]([CH:7]([C:9]([OH:11])=[O:10])[NH2:8])[CH2:5][C:4](=[O:12])[NH:3]1.[OH-].[Na+].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])O.[Na+]>O.O1CCOCC1>[CH2:15]([O:22][C:23]([NH:8][CH:7]([CH:6]1[CH2:5][C:4](=[O:12])[NH:3][C:2]1=[O:1])[C:9]([OH:11])=[O:10])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 130894332-(2,5-Dioxopyrrolidin-3-yl)glycine

Produkt 1

HCID 13105388Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

In 250 ml of water-dioxane (1:1) was suspended 10 g of 2-(2,5-dioxopyrrolidin-3-yl)glycine and under cooling at 0°-5° C. the above amino acid was dissolved by addition of 70 ml of 1 N sodium hydroxide. To this solution was added 15 ml of benzyloxycarbonyl chloride and, with adjusting pH to 7.1-7.4 with sodium hydrogen carbonate, the mixture was stirred at the same temperature as above for 2 hours. The reaction mixture was concentrated under reduced pressure to remove the organic solvent and the concentrate was washed with ethyl acetate. The aqueous layer was adjusted to pH 1 with conc. hydrochloric acid and allowed to stand in a refrigerator overnight to give crystals. Yield 15.8 g.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove the organic solvent
  3. washthe concentrate was washed with ethyl acetate
  4. customto stand in a refrigerator overnight
  5. customto give crystals

Quellen und Nachweise

ORD-Eintrag
ord-e4d12ecafb28404cb056b858859da1a8
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436918

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