Methyl iodide → HCID 178459476, compound
Reaction equation
[I:1][CH3:2].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([C:14]([N:16]([CH2:18][C:19]2[N:26]3[C:22]([S:23][CH:24]=[CH:25]3)=[CH:21][N:20]=2)[CH3:17])=[O:15])[CH2:12][C@H:11]([S:27][C:28]2[C@H:29]([CH3:45])[C@@H:30]3[C@@H:40]([C@H:41]([OH:43])[CH3:42])[C:39](=[O:44])[N:31]3[C:32]=2[C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]>>[I-:1].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([C:14]([N:16]([CH3:17])[CH2:18][C:19]2[N:20]([CH3:2])[CH:21]=[C:22]3[N+:26]=2[CH:25]=[CH:24][S:23]3)=[O:15])[CH2:12][C@H:11]([S:27][C:28]2[C@H:29]([CH3:45])[C@@H:30]3[C@@H:40]([C@H:41]([OH:43])[CH3:42])[C:39](=[O:44])[N:31]3[C:32]=2[C:33]([O:35][CH2:36][CH:37]=[CH2:38])=[O:34])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]Participants
Procedure
Iodomethane (0.84 g) is added to 37.0 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[N-(imidazo[5,1-b]thiazol-5-yl)methyl-N-methylaminocarbonyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate, and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 18 hr. The excess reagent is removed by evaporation under reduced pressure, and the residue is purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) to give 36.3 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[N-methyl-N-(6-methylimidazo[5,1-b]thiazolium-5-yl)methylaminocarbonyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide as a milky white 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-aa800e7ff84b4b759a2c0f3494d5c9da
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180622B2
Reaction notes
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