Ethanol → (4S)-4-(4-cyclohexylbenzylthio)-L-proline

HRID 1066202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066202
Cl.[SH:2][C@@H:3]1[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.[OH-].[Na+].[CH:13]1([C:19]2[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O)C>C(Cl)(Cl)Cl>[CH:13]1([C:19]2[CH:26]=[CH:25][C:22]([CH2:23][S:2][C@@H:3]3[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]3)=[CH:21][CH:20]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 133433651-(Chloromethyl)-4-cyclohexylbenzeneHCID 74890044(4S)-4-mercapto-L-proline hydrochloride

Produkt 1

HCID 68543958(4S)-4-(4-cyclohexylbenzylthio)-L-prolineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To (4S)-4-mercapto-L-proline hydrochloride (300 mg) is added 2 N sodium hydroxide (1.6 ml) aqueous solution, and the mixture is stirred at 0° C. A solution of 4-cyclohexylbenzyl chloride (340 mg) in a mixed solvent of ethanol (5 ml)/chloroform (1 ml) is added thereto, and the mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure, and deposited crystals are filtered off. The crystals are washed with water, ethanol and diethyl ether successively to give 470 mg (91%) of the titled compound.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature overnight
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. filtrationare filtered off
  4. washThe crystals are washed with water, ethanol and diethyl ether successively

Quellen und Nachweise

ORD-Eintrag
ord-2d30957efc5a4950a439d40b694b9fb3
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242476B1

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