Methanol → methyl N-(tert-butoxycarbonyl)glycylglycinate

HRID 1863466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1863466
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].CO.C(N(CC)CC)C.ClC1C=C(Cl)C(Cl)=CC=1[O:26][C:27](=O)[CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C)C=O>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:27](=[O:26])[CH2:28][NH:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 12799284t-Butoxycarbonylglycine-2,4,5-Trichlorophenyl Ester

Produkt 1

HCID 637608methyl N-(tert-butoxycarbonyl)glycylglycinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Prepare a solution of 1.98 g. of glycine methyl ester hydrochloride in dimethylformamide containing 8 ml. of methanol and 1.42 g. of triethylamine. Cool and stir the solution while adding 5.0 g. of t-butoxycarbonylglycine-2,4,5-trichlorophenyl ester in 25 ml. of dimethylformamide. Stir the reaction mixture overnight, filter and evaporate the filtrate to dryness under reduced pressure. Chromatograph the residue on 150 g. of silica gel and collect the desired product which is eluted by an ethyl acetate:chloroform (1:9) mixture. Evaporate the eluate to dryness and crystallize from hexane to obtain the title product (m.p. 132°-135° C.).

Aufarbeitung

  1. customPrepare a solution of 1.98 g
  2. temperatureCool
  3. additionwhile adding 5.0 g
  4. stirringStir the reaction mixture overnight
  5. filtrationfilter
  6. customevaporate the filtrate to dryness under reduced pressure
  7. customof silica gel and collect the desired product which
  8. washis eluted by an ethyl acetate:chloroform (1:9) mixture
  9. customEvaporate the eluate to dryness
  10. customcrystallize from hexane

Quellen und Nachweise

ORD-Eintrag
ord-442fb92c95e24a1fa5e17d9ac1377c25
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04169141

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