Methyl iodide → HCID 178459472, compound
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]3[CH:22]=[N:21][CH:20]=[C:17]3[S:18][CH:19]=2)[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].[OH:40][C@@H:38]([C@H:37]1[C:36](=[O:41])[N:28]2[C:29]([C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])=[C:25]([S:24][C@H:11]3[CH2:12][C@@H:13]([CH:14]([OH:23])[C:15]4[N+:16]5[C:17](=[CH:20][N:21]([CH3:2])[CH:22]=5)[S:18][CH:19]=4)[N:9]([C:7]([O:6][CH2:3][CH:4]=[CH2:5])=[O:8])[CH2:10]3)[C@H:26]([CH3:42])[C@H:27]12)[CH3:39]Participants
Procedure
Iodomethane (1.70 g) is added to 70.6 mg of allyl(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer A) described in Example 6-b), and the mixture is stirred in an argon atmosphere at room temperature in a light-shielded state for 14 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 83.4 mg of allyl(1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(6-methylimidazo[5,1-b]thiazolium-3-yl)methyl]pyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylate iodide (stereoisomer A) 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-f25eba3bc31845ae974c1e14618e8996
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06180622B2
Reaction notes
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