Methyl iodide → HCID 178459470, compound

HRID 1088641Notes

Reaction equation

HRID 1088641 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][N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1)=[O:6])[CH:2]=[CH2:3].[CH3:37][I:38]>CC(C)=O>[I-:38].[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][N+:32]1[CH:36]=[CH:35][N:34]([CH3:37])[CH:33]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 15086186HCID 15086186, compound

Product 1

HCID 178459470HCID 178459470, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(imidazol-1-yl)methylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (15.4 g), methyl iodide (18.6 ml) and acetone (80 ml) was stirred at ambient temperature for 5 hours. The reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (75 g) eluting with a mixture of dichloromethane and methanol (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(3-methyl-1-imidazolio)methylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate iodide (17.72 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe resulting residue was chromatographed on silica gel (75 g)
  3. washeluting with a mixture of dichloromethane and methanol (9:1, V/V)
  4. additionThe fractions containing the desired compound
  5. customwere collected
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-d71312f414834923a30b4c6914804596
Source dataset
uspto-grants-1990_10
Patent number
US04963544

Reaction notes

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