2-Fluoroethyl trifluoromethanesulfonate → HCID 178459458, compound
Reaction equation
[F:1][C:2]([F:11])([F:10])[S:3]([O:6][CH2:7][CH2:8][F:9])(=[O:5])=[O:4].[CH2:12]([O:15][C:16]([N:18]1[C@H:22]([CH2:23][C:24]2[S:28][C:27]3=[CH:29][N:30]=[CH:31][N:26]3[CH:25]=2)[CH2:21][C@H:20]([S:32][C:33]2[C@H:34]([CH3:50])[C@@H:35]3[C@@H:45]([C@H:46]([OH:48])[CH3:47])[C:44](=[O:49])[N:36]3[C:37]=2[C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[CH2:19]1)=[O:17])[CH:13]=[CH2:14]>>[F:1][C:2]([F:11])([F:10])[S:3]([O-:6])(=[O:5])=[O:4].[CH2:12]([O:15][C:16]([N:18]1[C@H:22]([CH2:23][C:24]2[S:28][C:27]3=[CH:29][N:30]([CH2:7][CH2:8][F:9])[CH:31]=[N+:26]3[CH:25]=2)[CH2:21][C@H:20]([S:32][C:33]2[C@H:34]([CH3:50])[C@@H:35]3[C@@H:45]([C@H:46]([OH:48])[CH3:47])[C:44](=[O:49])[N:36]3[C:37]=2[C:38]([O:40][CH2:41][CH:42]=[CH2:43])=[O:39])[CH2:19]1)=[O:17])[CH:13]=[CH2:14]Participants
Procedure
2-Fluoroethyl trifluoromethanesulfonate (76.4 mg) is added to 41.1 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-2-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate described in Example 23-a), and the mixture is stirred in an argon atmosphere at room temperature for 2 hr. The solvent is removed by evaporation under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol 1:1) to give 54.1 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[6-(2-fluoroethyl)imidazo[5,1-b]thiazolium-2-yl]methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate trifluoromethanesulfonate as a yellow viscous material.
Workup
- customThe solvent is removed by evaporation under reduced pressure
- customthe residue is purified by column chromatography on Sephadex
Sources & evidence
- ORD record
- ord-243e3d2047bb450cbd5c3fc83f484dee
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180622B2
Reaction notes
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