Methyl iodide → HCID 131710137, compound

HRID 1605501Notes

Reaction equation

HRID 1605501 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:22]([C@H:24]([C@@H:26]([OH:42])[C@@H:27]([CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[C:33]([OH:38])[C:32]=1[C:39]([OH:41])=[O:40])[CH3:28])[CH3:25])=[O:23])[C@H:4]1[O:8][C@@:7]([C@@H:11]2[O:16][C@@H:15]([CH3:17])[C@@:14]([OH:20])([CH2:18][CH3:19])[CH2:13][CH2:12]2)([CH2:9][CH3:10])[CH2:6][C@@H:5]1[CH3:21].[CH2:43](Cl)Cl.CI>[Ag]=O.CO>[CH3:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH2:29][CH:27]([CH3:28])[CH:26]([OH:42])[CH:24]([CH3:25])[C:22](=[O:23])[CH:3]([CH2:2][CH3:1])[CH:4]2[CH:5]([CH3:21])[CH2:6][C:7]([CH2:9][CH3:10])([CH:11]3[CH2:12][CH2:13][C:14]([CH2:18][CH3:19])([OH:20])[CH:15]([CH3:17])[O:16]3)[O:8]2)=[C:32]([C:39]([O:41][CH3:43])=[O:40])[C:33]=1[OH:38]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 6344DichloromethaneHCID 5360807Lasalocid

Product 1

HCID 131710137HCID 131710137, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6.2 g. of crystalline antibiotic X-537A in 125 ml. of methylene chloride was added 4.6 g. of silver oxide and 14 g. of methyl iodide. After stirring for 18 hours, the reaction mixture was filtered and the filtrate concentrated to 7.07 g. of a light yellow oil, which was decolorized with Darco, giving 6.09 g. of a colorless foam. A portion (4 g.) of the foam was chromatographed on a florisil column (150 g.) eluting with a gradient between methylene chloride (1 1.) to ether (1 1. ) and then ether (500 ml.) to acetone (500 ml.). Rechromatography of the slightly yellow oil, recovered from the florisil column, on a 75 g. silica gel column and eluting with a gradient between methylene chloride (1 1.) and 15% ether/methylene chloride gave 200 mg. of a clear viscous oil, Bp. 170°d/005 mm. [α]D25 -7.19°, (1.1%, CH3OH).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated to 7.07 g
  3. customgiving 6.09 g
  4. customA portion (4 g.) of the foam was chromatographed on a florisil column (150 g.)
  5. washeluting with a gradient between methylene chloride (1 1.) to ether (1 1. )
  6. customRechromatography of the slightly yellow oil, recovered from the florisil column, on a 75 g
  7. washsilica gel column and eluting with a gradient between methylene chloride (1 1.) and 15% ether/methylene chloride
  8. customgave 200 mg

Sources & evidence

ORD record
ord-cfcf9faeb41a49039bf00b176b31dbee
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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