Ethyl chloroformate → HCID 20379307, Verbindung

HRID 2051615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2051615
ClC(OCC)=O.[C:7]([O:11][C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].I.[NH:20]=[C:21]1[N:25]([CH3:26])[CH2:24][CH2:23][S:22]1>C(Cl)Cl.C(N(CC)CC)C>[CH3:26][N:25]1[CH2:24][CH2:23][S:22][C:21]1=[N:20][C:16](=[O:18])[CH2:15][NH:14][C:12]([O:11][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:13]

Komponenten

6

Edukt 3

HCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27705073-Methyl-1,3-thiazolidin-2-imine hydroiodide

Produkt 1

HCID 20379307HCID 20379307, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Ethyl chloroformate (0.25 ml.) at -5° C. was added to a solution of 350 mg. of t-butoxycarbonylaminoacetic acid and 0.4 ml. of triethylamine in 10 ml. of methylene chloride at -5° C. After stirring 5 minutes at -5° C. there was added a solution of 610 mg. of 2-imino-3-methylthiazolidine hydrogen iodide and 1.0 ml. of triethylamine in 10 ml. of methylene chloride also at -5° C. Stirring was continued at -5° C. for 15 minutes and one hour at room temperature. The reaction mixture was washed with 40 ml. of 20% (w/v) citric acid solution, sodium bicarbonate solution, and water, dried and concentrated to dryness. The residue was triturated with ether, petroleum ether and ether and finally collected to give pure N-(3-methylthiazolidin-2-ylidene)-t-butoxycarbonylaminoacetamide.

Aufarbeitung

  1. customat -5° C
  2. additionthere was added a solution of 610 mg
  3. customalso at -5° C
  4. stirringStirring
  5. waitwas continued at -5° C. for 15 minutes and one hour at room temperature
  6. washThe reaction mixture was washed with 40 ml
  7. dry with materialof 20% (w/v) citric acid solution, sodium bicarbonate solution, and water, dried
  8. concentrationconcentrated to dryness
  9. customThe residue was triturated with ether, petroleum ether and ether
  10. customfinally collected

Quellen und Nachweise

ORD-Eintrag
ord-282b45b8f3454126bcf896e4c191b799
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04181661

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