Benzyl chloroformate → (2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acid

HRID 36537

Reaktionsgleichung

Reaktionsgleichung von HRID 36537
C[Si](N([Si](C)(C)C)C(=O)C(F)(F)F)(C)C.[NH2:16][C@@H:17]([CH2:21][C:22]#[N:23])[C:18]([OH:20])=[O:19].[CH2:24]([O:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:25]1([CH2:24][O:31][C:32]([NH:16][C@@H:17]([CH2:21][C:22]#[N:23])[C:18]([OH:20])=[O:19])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 4397423-cyano-L-alanine

Produkt 1

HCID 12771373(2S)-2-{[(Benzyloxy)carbonyl]amino}-3-cyanopropanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Bis (trimethylsilyl)trifluoroacetamide (9.4 mL, 35 mmol.) was added to a suspension of (αS)-amino-3-cyanopropanoic acid (2.0 g., 17.5 mmol.) in 10 mL of dry acetonitrile and the reaction mixture was stirred for 3 hours. Benzylchloroformate (2.5 mL, 17.5 mmol) was added, the reaction mixture was stirred overnight, concentrated in vacuo, and dissolved in ethyl acetate (200 mL). The organic solution was washed with water (2×) and brine, dried (Na2SO4), and concentrated in vacuo. Crystallization from isopropyl ether yielded 3.82 g. of the title A product.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in ethyl acetate (200 mL)
  4. washThe organic solution was washed with water (2×) and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customCrystallization from isopropyl ether
  8. customyielded 3.82 g

Quellen und Nachweise

ORD-Eintrag
ord-ee7f8a7636b943b6be7f4ce24c5ab941
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05414017

Verknüpfte Notizen

Wird geladen…