Sodium Chloride → (2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine

HRID 5114

Reaction equation

I[CH2:2][CH2:3][OH:4].C(=O)(O)[O-].[Na+].[CH3:10][O:11][C:12]1[CH:28]=[CH:27][C:15]([CH2:16][S:17][C@@H:18]2[CH2:22][NH:21][C@H:20]([C:23](=[O:26])[NH:24][CH3:25])[CH2:19]2)=[CH:14][CH:13]=1.[Cl-].[Na+]>CN(C)C=O>[OH:4][CH2:3][CH2:2][N:21]1[CH2:22][C@@H:18]([S:17][CH2:16][C:15]2[CH:27]=[CH:28][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH2:19][C@H:20]1[C:23](=[O:26])[NH:24][CH3:25]

Participants

Conditions

Temperature: 40 °C

Procedure

934 μl of 2-iodoethanol and 1.01 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 2.80 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 18 ml of dry dimethylformamide, and the mixture was stirred at 40° C. for 24 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 15:1 by volume mixture of ethyl acetate and methanol), to afford 2.22 g of the title compound as colorless crystals, melting at 88°-89.5° C.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with an aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was then removed by distillation under reduced pressure
customthe residue was purified by column chromatography through silica gel (
washeluted with a 15:1 by volume mixture of ethyl acetate and methanol),

Sources & evidence

ORD record: ord-c4d3c967ee794540a87c6456700647c8
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05242914

Linked notes

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