Glycine ethyl ester → N-formyl-L-phenylalanyl-glycine ethyl ester

HRID 1580548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1580548
[CH:1]([NH:3][C@H:4]([C:12]([OH:14])=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:2].[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[CH3:16].C([N+]#[C-])(C)(C)C>O1CCOCC1>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH:20][C:12](=[O:14])[C@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:3][CH:1]=[O:2])[CH3:16]

Komponenten

5

Edukt 3

HCID 12176Glycine ethyl esterHCID 23577Tert-Butyl isocyanideHCID 759256N-Formyl-L-phenylalanine

Produkt 1

HCID 12052887N-formyl-L-phenylalanyl-glycine ethyl esterAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3.9 g (20 mM) N-formyl-L-phenylalanine, 2.5 g (24 mM) glycine ethyl ester, and 1.7 g (20 mM) tert-butyl isonitrile in 30 ml dioxane was heated at 40°-50°C for 28 hours. It was then evaporated to dryness, and the residue was dissolved in 300 ml methylene chloride. The solution was washed as in the preceding examples, dried, and evaporated. The residue was crystallized from carbon tetrachloride and petroleum ether to produce 3.1 g N-formyl-L-phenylalanyl-glycine ethyl ester (48 percent yield based on the glycine ethyl ester).

Aufarbeitung

  1. customIt was then evaporated to dryness
  2. dissolutionthe residue was dissolved in 300 ml methylene chloride
  3. customdried
  4. customevaporated
  5. customThe residue was crystallized from carbon tetrachloride and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-61d9af6085214577b7e9b36f5073a691
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03933783

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