4-Toluenesulfonyl chloride → (2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 1855923

Reaktionsgleichung

Reaktionsgleichung von HRID 1855923
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>O.CCOCC>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 145742L-Proline

Produkt 1

HCID 691957(2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acidAusbeute 74,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In this example, L-proline (11.5 g; 0.10 mole) and caustic soda (8.0 g; 0.2 moles) are dissolved in 100 ml water, and a solution of p-methylphenylsulfonyl chloride (20.9 g) dissolved in ether (80 ml) is added thereto with vigorous stirring under cooling in an ice bath (5°-10° C.). After reaction for about 5 hours, the reaction mixture is left standing, and the upper ether layer is removed. The remaining aqueous layer is admixed with 2N hydrochloric acid to adjust the pH to 3-4. After being left standing in a cool place (0°-5° C.), the deposited crystals are filtered off. The crystals are recrystallized from an aqueous 60% ethanol solution (about 200 ml), whereby p-methylphenylsulfonyl-L-proline (compound number 15; 20.1 g; m.p. 57°-59° C.) was obtained. Yield: 70%.

Aufarbeitung

  1. additionis added
  2. temperatureunder cooling in an ice bath (5°-10° C.)
  3. customAfter reaction for about 5 hours
  4. waitthe reaction mixture is left
  5. customthe upper ether layer is removed
  6. waitAfter being left
  7. customstanding in a cool place (0°-5° C.)
  8. filtrationthe deposited crystals are filtered off
  9. customThe crystals are recrystallized from an aqueous 60% ethanol solution (about 200 ml)

Quellen und Nachweise

ORD-Eintrag
ord-13e9f9304d2b430b92bb2a939109ab3f
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04217130

Verknüpfte Notizen

Wird geladen…