Methyl iodide → HCID 131722344, compound

HRID 568247Notes

Reaction equation

[I:1][CH3:2].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH2:14][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:23][C:24]2[C@H:25]([CH3:41])[C@@H:26]3[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]>>[I-:1].[CH2:3]([O:6][C:7]([N:9]1[C@H:13]([CH2:14][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:23][C:24]2[C@H:25]([CH3:41])[C@@H:26]3[C@@H:36]([C@H:37]([OH:39])[CH3:38])[C:35](=[O:40])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])[CH2:10]1)=[O:8])[CH:4]=[CH2:5]

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 131722346HCID 131722346, compound

Product 1

HCID 131722344HCID 131722344, compound

Procedure

Iodomethane (0.468 ml) is added to 43.0 mg of allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(imidazo[5,1-b]thiazol-7-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate described in Example 34-a), and the mixture is stirred in an argon atmosphere in a light-shielded state at room temperature for 19 hr. The excess reagent is removed by evaporation under reduced pressure to give a crude product of allyl(1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-(6-methylimidazo[5,1-b]thiazolium-7-yl)methylpyrrolidin-3-yl]thio-6-((1R)-1-hydroxyethyl)-1-methylcarbapen-2-em-3-carboxylate iodide. The procedure of Example 11-b) is repeated, except that the whole quantity of the crude product prepared just above is used. Thus, 3.2 mg of the title compound is obtained.

Workup

customThe excess reagent is removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-78f7b6a9b3a64cb6ab5413ca78020b34
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180622B2

Reaction notes

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