Reaction equation
[C:1]([CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9][N:8]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])(=[O:3])[NH2:2].[C:30]([SH:33])(=[O:32])[CH3:31].[H-].[Na+].O>CN(C)C=O>[C:30]([S:33][C@@H:10]1[CH2:9][N:8]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[C@H:7]([CH2:6][O:5][CH2:4][C:1](=[O:3])[NH2:2])[CH2:11]1)(=[O:32])[CH3:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2S,4R)-2-(carbamoylmethyl)oxymethyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.98 g) in dimethylformamide (2 ml) was added to a reaction mixture of thioacetic S-acid (0.25 ml) and sodium hydride (62.8% in oil suspension) (0.11 g) in dimethylformamide (10 ml) in a nitrogen stream and the mixture was heated at 70°-75° C. for 3 hours. The mixture was poured into water (100 ml), extracted with ethyl acetate (50 ml×3), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with a mixture of methanol and chloroform (1:99 v/v) to give (2S,4S)-4-acetylthio-2-(carbamoylmethyl)oxymethyl-1-(4nitrobenzyloxycarbonyl)pyrrolidine (0.72 g).
Workup
- temperaturethe mixture was heated at 70°-75° C. for 3 hours
- extractionextracted with ethyl acetate (50 ml×3)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto give a syrup
- washeluted with a mixture of methanol and chloroform (1:99 v/v)
Sources & evidence
- ORD record
- ord-b94970bc0f7442e0ba8aa0e72eeb890f
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05061804
Linked notes
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