Methyl iodide → HCID 178459467, compound

HRID 975720Notes

Reaction equation

HRID 975720 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH2:38][OH:39])=[O:6])[CH:2]=[CH2:3].[CH3:40][I:41]>CC(C)=O>[I-:41].[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27][CH2:28][CH:29]=[CH2:30])=[O:26])[CH2:9][C@H:8]1[CH2:31][CH2:32][N+:33]1[CH:37]=[CH:36][N:35]([CH3:40])[C:34]=1[CH2:38][OH:39])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57011048HCID 57011048, compound

Product 1

HCID 178459467HCID 178459467, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(2-hydroxymethylimidazol-1-yl)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (3.02 g) in acetone (15 ml) was added methyl iodide (3.36 ml) at room temperature and the solution was allowed to stand for 6 hours. The solvent was evaporated to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(2-hydroxymethyl-3-methyl-1-imidazolio)ethyl}-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (3.75 g) as a yellow solid. This compound was immediately used as the starting compound for the next step.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1ab2adfce81d4977aa3e33bddc67bda3
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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