Benzyl chloroformate → (2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

HRID 1728308

Reaktionsgleichung

Reaktionsgleichung von HRID 1728308
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[OH-].[Na+]>O>[CH2:14]([O:13][C:11]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 83887D-Aspartic Acid

Produkt 1

HCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

D-Aspartic acid (25.0 g, 0.188 mol) and benzyl chloroformate (34.3 ml, 0.282 mol) were added to sodium hydroxide (22.9 g, 0.564 mol) in water (600 ml). The resulting mixture was stirred at room temperature for 3 days. The mixture was then acidified with 6MHCl to pH1 and extracted with ethyl acetate (3×250 ml). The extracts were combined, dried (MgSO4) and evaporated to a clear oil, wt 50.2 g. 1H NMR (90 MHz, CDCl3): δ 3.05 (2,bm), 4.65 (1,bm), 5.25 (2,s), 6.2 (1,bs), 7.4 (5,s), 10 (1,bs).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×250 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated to a clear oil, wt 50.2 g

Quellen und Nachweise

ORD-Eintrag
ord-7f892152271b4d709277c712b0bf43c3
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326756

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