Triethylamine → N-t-butoxycarbonyl-L-alanyl-D-alanine benzyl ester

HRID 35713

Reaktionsgleichung

Reaktionsgleichung von HRID 35713
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:25]([O:32][C:33](=[O:37])[C@@H:34]([CH3:36])[NH2:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:25]([O:32][C:33](=[O:37])[C@@H:34]([CH3:36])[NH:35][C:11](=[O:13])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 2802425D-Alanine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

Produkt 1

HCID 13369188N-t-butoxycarbonyl-L-alanyl-D-alanine benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 23.0 g. (0.121 m) of N-t-butoxycarbonyl-L-alanine, 42.6 g. (0.121 m) of D-alanine benzyl ester p-toluenesulfonic acid salt and 17 ml. (0.121 m) of triethylamine in 400 ml. of cold (0° C.) methylene chloride was added dropwise 25.0 g. (0.121 m) of dicyclohexylcarbodiimide in 100 ml. of methylene chloride. After stirring overnight at room temperature the solids were filtered and the filtrate concentrated to an oil. The residue was dissolved in 400 ml. of ethyl acetate which was washed with a 1% hydrochloric acid solution, a 10% potassium carbonate solution, water and a brine solution. The organic phase was separated, dried over magnesium sulfate and concentrated to an oil. The residue was triturated with diethyl ether and the resulting solids filtered under nitrogen, 16.0 g. An additional 12.7 g. of the desired product crystallized from the filtrate.

Aufarbeitung

  1. filtrationwere filtered
  2. concentrationthe filtrate concentrated to an oil
  3. dissolutionThe residue was dissolved in 400 ml
  4. washof ethyl acetate which was washed with a 1% hydrochloric acid solution
  5. customThe organic phase was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to an oil
  8. customThe residue was triturated with diethyl ether
  9. filtrationthe resulting solids filtered under nitrogen
  10. customof the desired product crystallized from the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-8a2f92c2d143402187baa2f3871614ad
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767743

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