Methyl iodide → allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-7-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide
Reaction equation
[I:1][CH3:2].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH:14]([OH:23])[C:15]2[N:16]=[CH:17][N:18]3[CH:22]=[CH:21][S:20][C:19]=23)[CH2:12][C@H:11]([S:24][C:25]2[C@H:26]([CH3:42])[C@@H:27]3[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:28]3[C:29]=2[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]>>[I-:1].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH:14]([OH:23])[C:15]2[N:16]([CH3:2])[CH:17]=[N+:18]3[CH:22]=[CH:21][S:20][C:19]=23)[CH2:12][C@H:11]([S:24][C:25]2[C@H:26]([CH3:42])[C@@H:27]3[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:28]3[C:29]=2[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]Participants
Procedure
Iodomethane (2.13 g) is added to 177 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-7-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate prepared in Example 14-b), and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 12 hr. The excess reagent is removed by evaporation under reduced pressure. The residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 206 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-7-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide (a diastereomer mixture) as a light yellow amorphous material.
Workup
- customThe excess reagent is removed by evaporation under reduced pressure
- customThe residue is purified by column chromatography on Sephadex
Sources & evidence
- ORD record
- ord-0cbfdef61bbe45e185781944104f9211
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180622B2
Reaction notes
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