Cysteamine → (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-thiazolin-2-yl)pyrrolidine
Reaction equation
[C:1]([C@@H:3]1[CH2:7][C@@H:6]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH2:5][N:4]1[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:14])#[N:2].N[CH2:27][CH2:28][SH:29]>O1CCCC1>[CH3:12][S:9]([O:8][C@H:6]1[CH2:5][N:4]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])[C@H:3]([C:1]2[S:29][CH2:28][CH2:27][N:2]=2)[CH2:7]1)(=[O:11])=[O:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2S,4R)-2-cyano-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2 g) in tetrahydrofuran (40 ml) was added 2-aminoethanethiol (630 mg) at ambient temperature. After stirring for 24 hours at the same temperature, the mixture was evaporated. The residue was extracted with dichloromethane, washed with water and brine successively, and dried over magnesium sulfate. The organic layer was evaporated, and then the obtained oil was subjected to a column chromatography on silica gel and eluted with a mixture of dichloromethane and acetone (4:1,V/V) to give (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(2-thiazolin-2-yl)pyrrolidine (0.96 g).
Workup
- customthe mixture was evaporated
- extractionThe residue was extracted with dichloromethane
- washwashed with water and brine successively
- dry with materialdried over magnesium sulfate
- customThe organic layer was evaporated
- washeluted with a mixture of dichloromethane and acetone (4:1,V/V)
Sources & evidence
- ORD record
- ord-5da82f8130e749c7ba68502331bd2e8e
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05138064
Reaction notes
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