Methyl iodide → HCID 178459471, compound

HRID 568236Notes

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[S:19][C:18]3=[CH:20][N:21]=[CH:22][N:17]3[CH:16]=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[S:19][C:18]5=[CH:20][N:21]([CH3:2])[CH:22]=[N+:17]5[CH:16]=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

Reactant 2

HCID 6328Methyl iodide

HCID 131722323HCID 131722323, compound

Product 1

HCID 178459471HCID 178459471, compound

Procedure

Iodomethane (0.6 ml) is added to 54.0 mg of allyl (1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate (stereoisomer A) described in Example 16-a), and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 5 hr. The excess reagent is removed by evaporation under reduced pressure to give 68.9 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-2-yl)methyl]pyrrolidin-3-yl]thio-1-methylcarbapen-2-em-3-carboxylate iodide (stereoisomer A) as a slightly yellow amorphous material.

Workup

customThe excess reagent is removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-b1a585d0f68e4bd8a684d2e4fc0ad093
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180622B2

Reaction notes

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