Methyl iodide → HCID 178459468, compound

HRID 975723Notes

Reaction equation

HRID 975723 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[C:37]([CH2:38][O:39][CH3:40])=[CH:36][N:35]=[CH:34]1)=[O:6])[CH:2]=[CH2:3].[CH3:41][I:42]>CC(C)=O>[I-:42].[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[C:37]([CH2:38][O:39][CH3:40])=[CH:36][N:35]([CH3:41])[CH:34]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 56998199HCID 56998199, compound

Product 1

HCID 178459468HCID 178459468, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(5-methoxymethylimidazol-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 (1.79 g) in acetone (9.0 ml) was added methyl iodide (1.9 ml) at room temperature and the solution was allowed to stand for 3.5 hours. The solvent was evaporated to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(5-methoxymethyl-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 (2.24 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-f2f3a9b0cf894fa9b84c331414416c0a
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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