Methyl iodide → HCID 178459470, compound

HRID 1613999Notes

Reaction equation

HRID 1613999 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 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 vacu 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 vacu

Sources & evidence

ORD record
ord-72af992bc8ac4baf8977450e4f6302d7
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

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