Methyl iodide → HCID 178459465, compound

HRID 975716Notes

Reaction equation

HRID 975716 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][CH2:33][N:34]1[CH:38]=[CH:37][N:36]=[CH:35]1)=[O:6])[CH:2]=[CH2:3].[CH3:39][I:40]>CC(C)=O>[I-:40].[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][CH2:33][N+:34]1[CH:38]=[CH:37][N:36]([CH3:39])[CH:35]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 57145444HCID 57145444, compound

Product 1

HCID 178459465HCID 178459465, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{3-(imidazol-1-yl)propyl}pyrrolidin-4yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (4.00 g) in acetone (20 ml) was added methyl iodide (4.57 ml) at room temperature and the solution was allowed to stand overnight. The solvent was evaporated to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{3-(3-methyl-1-imidazolio) propyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (5.01 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-9900304fbfa2471c822731fc6477a90d
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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