Triethylamine → (2S, 4S)-1-(2-Methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

HRID 5115

Reaktionsgleichung

Reaktionsgleichung von HRID 5115
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][CH2:15][N:16]1[CH2:20][C@@H:19]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH2:18][C@H:17]1[C:31](=[O:34])[NH:32][CH3:33]>O1CCCC1>[CH3:8][S:9]([O:13][CH2:14][CH2:15][N:16]1[CH2:20][C@@H:19]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH2:18][C@H:17]1[C:31](=[O:34])[NH:32][CH3:33])(=[O:11])=[O:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14880306(2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Produkt 1

HCID 57207810(2S, 4S)-1-(2-Methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.06 ml of triethylamine and subsequently 584 μl of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 2.13 g of (2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 45 ml of dry tetrahydrofuran, and the mixture was stirred at 0° to 5° C. for 30 minutes. At the end of this time, the crystals which precipitated were collected by filtration and washed with tetrahydrofuran. The filtrate and washings were combined and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure, to afford 2.50 g of the title compound as an oil.

Aufarbeitung

  1. customAt the end of this time, the crystals which precipitated
  2. filtrationwere collected by filtration
  3. washwashed with tetrahydrofuran
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4ffa53c53ad4c46a62aa45858110c76
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242914

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