Hydrochloric Acid → (2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([CH2:9][O:10][CH2:11][C@@H:12]1[CH2:16][C@@H:15]([OH:17])[CH2:14][N:13]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1)=[O:19])([OH:8])=[O:7].C(N(CC)CC)C.Cl>ClCCl.O>[C:6]([CH2:9][O:10][CH2:11][C@@H:12]1[CH2:16][C@@H:15]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14][N:13]1[C:18]([O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=1)=[O:19])([OH:8])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of methanesulfonyl chloride (0.62 ml) in dichloromethane (2 ml) was dropwise added to a solution of (2S,4R)-2-(carboxymethyloxymethyl)-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.42 g) and triethylamine (1.4 ml) in dichloromethane (14 ml) at 0°-5° C. and the mixture was stirred at the same temperature for 1 hour. The mixture was poured into water (50 ml), adjusted to pH 2.5 with 6N hydrochloric acid and extracted with dichloromethane (50 ml×2). The organic layer was washed with brine, 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,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.30 g).
Workup
- extractionextracted with dichloromethane (50 ml×2)
- washThe organic layer was washed with brine
- 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-d122dbed595844feb3145e7c9c51806e
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04822787
Reaction notes
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