Hydrochloric Acid → HCID 14858826, Verbindung

HRID 1073981Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073981
[NH2:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3].[C:14]1([CH3:26])[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:15]=1[S:22](Cl)(=[O:24])=[O:23].O.Cl>[OH-].[Na+].O1CCOCC1>[C:14]1([CH3:26])[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:15]=1[S:22]([NH:1][C@H:2]([C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5])[CH3:3])(=[O:23])=[O:24]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 130462-Mesitylenesulfonyl chlorideHCID 83525L-Alanyl-L-proline

Produkt 1

HCID 14858826HCID 14858826, VerbindungAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

L-alanyl-L-proline (1.86 g, 10 mmole) was dissolved in aqueous sodium hydroxide (10 ml)-dioxane (10 ml), and dioxane (5 ml) solution of mesitylenesulfonylchloride (2.19 g, 10 mmole) was added dropwise to the solution while cooling and stirring while keeping pH value thereof to 10 to 11 with 1N aqueous sodium hydroxide. After that; the mixture was stirred further for 2 hours at room temperature. Water (20 ml) was added thereto and the mixture thus obtained was washed with diethyl ether (40 ml). The water layer was filtered and the filtrate thus obtained was adjusted to pH 2.0 with 1N hydrochloric acid while cooling and stirring to precipitate white solid material. The material was dissolved in 0.5N aqueous sodium hydroxide and the solution thus obtained was crystallized by addition of 1N aqueous hydrochloric acid to give N-mesitylenesulfonyl-L-alanyl-L-proline yield: 1.67 g, 45.3%).

Aufarbeitung

  1. additionwas added dropwise to the solution
  2. temperaturewhile cooling
  3. stirringthe mixture was stirred further for 2 hours at room temperature
  4. customthe mixture thus obtained
  5. washwas washed with diethyl ether (40 ml)
  6. filtrationThe water layer was filtered
  7. customthe filtrate thus obtained
  8. temperaturewhile cooling
  9. stirringstirring
  10. customto precipitate white solid material
  11. dissolutionThe material was dissolved in 0.5N aqueous sodium hydroxide
  12. customthe solution thus obtained
  13. customwas crystallized by addition of 1N aqueous hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-ee566e0950fc49afb6f1abac4eb7773d
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971993

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