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

HRID 1030176Notes

Reaction equation

HRID 1030176 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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-methylcarbamoyl-pyrrolidine 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.

Workup

  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

Sources & evidence

ORD record
ord-597f09037b874a6f88e1a2e71e19951d
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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