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:34])[N:31]([CH3:33])[CH3:32])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:32][N:31]([CH3:33])[C:30]([C@@H:16]1[CH2:17][C@H:18]([S:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH2:19][NH:15]1)=[O:34]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1 ml of a 4N dioxane solution of hydrogen chloride was added, whilst ice-cooling, to a solution of 385 mg of (2S, 4S)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (3) above] dissolved in 1 ml of ethyl acetate, and the mixture was stirred at room temperature for 1.5 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 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 1:2 by volume mixture of ethyl acetate and methanol), to afford 163 mg of the title compound as an oil.
Workup
- extractionit was extracted 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 1:2 by volume mixture of ethyl acetate and methanol),
Sources & evidence
- ORD record
- ord-e08bf8780bbe4cf28c4a3bcbffc10d69
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05242914
Linked notes
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