Methyl iodide → HCID 86750484, compound

HRID 975724Notes

Reaction equation

HRID 975724 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]=[C:36]([CH2:38][C:39](=[O:41])[NH2:40])[N:35]=[CH:34]1)=[O:6])[CH:2]=[CH2:3].[CH3:42][I:43]>CC(C)=O>[I-:43].[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]=[C:36]([CH2:38][C:39](=[O:41])[NH2:40])[N:35]([CH3:42])[CH:34]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86750486HCID 86750486, compound

Product 1

HCID 86750484HCID 86750484, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-carbamoylmethylimidazol-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 (1.08 g) in acetone (5.4 ml) was added methyl iodide (1.15 ml) at room temperature and the solution was allowed to stand for 5.5 hours. The solvent was evaporated to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(4-carbamoylmethyl-3-methyl-1-imidazolio)ethyl}pyrrolidin-4yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (1.31 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-a0c0d80e4db04fdc90f423164d33a0d6
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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