4-Chlorobenzenesulfonyl chloride → (2S,4S)-1-[2-[(4-chlorophenyl)sulfonyloxy]acetyl]-4-fluoropyrr olidine-2-carbonitrile
Reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:10])[CH2:8][OH:9])[C@H:4]([C:11]#[N:12])[CH2:3]1.C(N(CC)CC)C.Cl.CN(C)C.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>O.C(#N)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([O:9][CH2:8][C:7]([N:5]2[CH2:6][C@@H:2]([F:1])[CH2:3][C@H:4]2[C:11]#[N:12])=[O:10])(=[O:34])=[O:33])=[CH:28][CH:27]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
(2S,4S)-4-fluoro-1-(2-hydroxyacetyl)pyrrolidine-2-carboni trile (259 mg), triethylamine (0.42 mL), trimethylamine hydrochloride (143 mg) and acetonitrile (5 mL) were mixed together. While this mixture was cooled in a salt-ice bath, 4-chlorobenzenesulfonyl chloride (350 mg) was added in portions and the mixture was further stirred for 1 hour. Subsequently, water (5 mL) was added and the mixture was extracted with ethyl acetate (2×30 mL). The ethyl acetate extracts were combined, washed with saturated brine (2×5 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate) to give (2S,4S)-1-[2-[(4-chlorophenyl)sulfonyloxy]acetyl]-4-fluoropyrr olidine-2-carbonitrile as a white solid (256 mg, 49% yield).
Workup
- temperatureWhile this mixture was cooled in a salt-ice bath
- extractionthe mixture was extracted with ethyl acetate (2×30 mL)
- washwashed with saturated brine (2×5 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified on a silica gel column (eluant=ethyl acetate)
Sources & evidence
- ORD record
- ord-7527afd772754b6594c8965566b7398f
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915427B2
Reaction notes
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