Hydrochloric Acid → (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

HRID 5074Notes

Reaction equation

HRID 5074 reaction equation
O1CCOCC1.Cl.C(OC([N:15]1[CH2:19][C@@H:18]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:17][C@H:16]1[C:30](=[O:33])[NH:31][CH3:32])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][S:20][C@@H:18]2[CH2:19][NH:15][C@H:16]([C:30](=[O:33])[NH:31][CH3:32])[CH2:17]2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 57062218(2S, 4S)-1-(t-Butoxycarbonyl)-4-(4-methoxybenzyl-thio)-2-methylcarbamoylpyrrolidine

Product 1

HCID 14880277(2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidineYield 79.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

52.5 ml of a 4N dioxane solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 4.00 g of (2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine [prepared as described in step (3) above] dissolved in 50 ml of ethyl acetate. The mixture was stirred at 0° to 50° C. for 30 minutes and then at room temperature for 2 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate to make it weakly basic, and it was then extracted with ethyl acetate. The aqueous layer was saturated with ammonium chloride and then extracted with tetrahydrofuran. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 mixture by volume of ethyl acetate and methanol), to afford 2.34 g of the title compound as colorless crystals, melting at 53°-54° C.

Workup

  1. waitat room temperature for 2 hours
  2. extractionit was then extracted with ethyl acetate
  3. extractionextracted with tetrahydrofuran
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel (
  8. washeluted with a 5:1 mixture by volume of ethyl acetate and methanol),

Sources & evidence

ORD record
ord-0e70b857ff5341b6b9e0f7b265b239d3
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Reaction notes

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