1-(4-Benzylthiobutanoyl)-L-proline → 4-mercaptobutanoyl-L-proline

HRID 2071388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2071388
C([S:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])C1C=CC=CC=1>O.N>[SH:8][CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13]

Komponenten

4

Edukt 1

HCID 700744061-(4-Benzylthiobutanoyl)-L-proline

Produkt 1

HCID 228203034-mercaptobutanoyl-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 222AmmoniaLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

1-(4-Benzylthiobutanoyl)-L-proline (1.08 g.) is dissolved in a mixture of water (4 ml.) and concentrated ammonia (2.7 ml.). After 1 hour stirring at room temperature, the mixture is diluted with water, filtered, extracted with ethyl acetate, and the aqueous phase was concentrated in vacuo. This ammonium salt of 1-(4-mercaptobutanoyl)-L-proline is purified by ion exchange chromatography on a column of diethyl-aminoethyl-Sephadex(cross linked dextran) with a gradient of ammonium bicarbonate, yield 0.7 g. The ammonium salt is dissolved in water (2ml.) and applied to a column of Dowex 50 sulfonic acid resin (analytical grade) in the hydrogen form, and the free acid is eluted with water. The fractions containing the desired material (sulfhydryl reagent and carboxyl reagent positive) are pooled and freeze dried to obtain 1-(4-mercaptobutanoyl)-L-proline.

Aufarbeitung

  1. filtrationfiltered
  2. extractionextracted with ethyl acetate
  3. concentrationthe aqueous phase was concentrated in vacuo
  4. customThis ammonium salt of 1-(4-mercaptobutanoyl)-L-proline is purified by ion exchange chromatography on a column of diethyl-aminoethyl-Sephadex(cross linked dextran) with a gradient of ammonium bicarbonate, yield 0.7 g
  5. dissolutionThe ammonium salt is dissolved in water (2ml.)
  6. washthe free acid is eluted with water
  7. additionThe fractions containing the desired material (sulfhydryl reagent and carboxyl reagent positive)
  8. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-16a80f7264324dcd8d298949e8ae976e
Quelldatensatz
uspto-grants-1977_09
Patentnummer
US04046889

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