Hydrochloric Acid → (2S)-1-[N-(4-Chlorobenzylaminocarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]pyrrolidine

HRID 1720513Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720513
ClC(OC(Cl)(Cl)Cl)=O.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.Cl.ClC1C=CC(OCC([C@@H]2CCCN2C(=O)[C@@H]2CCCN2)O)=CC=1.C([O:46][C:47]([N:49]1[CH2:71][CH2:70][CH2:69][C@H:50]1[C:51]([N:53]1[CH2:57][CH2:56][CH2:55][C@H:54]1[CH:58]([OH:68])[CH2:59][O:60][C:61]1[CH:66]=[CH:65][C:64]([Cl:67])=[CH:63][CH:62]=1)=[O:52])=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1.C(Cl)Cl.C(N(CC)CC)C>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:47]([N:49]2[CH2:71][CH2:70][CH2:69][C@H:50]2[C:51]([N:53]2[CH2:57][CH2:56][CH2:55][C@H:54]2[CH:58]([OH:68])[CH2:59][O:60][C:61]2[CH:62]=[CH:63][C:64]([Cl:67])=[CH:65][CH:66]=2)=[O:52])=[O:46])=[CH:12][CH:11]=1

Komponenten

10

Edukt 5

HCID 313Hydrochloric AcidHCID 10426DiphosgeneHCID 660364-ChlorobenzylamineHCID 67771535(2S)-1-[N-(tert-butoxycarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-l-hydroxyethyl]pyrrolidineHCID 67771646(2S)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]-1-(L-prolyl)pyrrolidine hydrochloride

Produkt 1

HCID 67771067(2S)-1-[N-(4-Chlorobenzylaminocarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of trichloromethyl chloroformate (0.35 ml) THF (40 ml) was dropwise added a solution of 4-chlorobenzylamine (0.71 ml) and triethylamine (0.81 ml) in THF (20 ml) under ice-cooling, and the mixture was stirred at room temperature for 1.5 hours. A suspension of (2S)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]-1-(L-prolyl)pyrrolidine hydrochloride which had been obtained by treating (2S)-1-[N-(tert-butoxycarbonyl)-L-prolyl]-2-[2-(4-chlorophenoxy)-l-hydroxyethyl]pyrrolidine (2.13 g) with 4N hydrochloric acid in 1,4-dioxane (20 ml), and triethylamine (0.81 ml) in methylene chloride (20 ml) was dropwise added to the reaction mixture, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: chloroform-methanol) to give 2.09 g of the title compound.

Aufarbeitung

  1. temperaturecooling
  2. customhad been obtained
  3. additionwas dropwise added to the reaction mixture
  4. stirringby stirring at room temperature for 1 hour
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 1N hydrochloric acid, saturated aqueous solution of sodium bicarbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (eluate: chloroform-methanol)

Quellen und Nachweise

ORD-Eintrag
ord-8396440d29674d1992a6c27d4a990e63
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506256

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