Acetone → HCID 68118329, compound

HRID 1730630Notes

Reaction equation

HRID 1730630 reaction equation
[CH2:1]([S:3][CH2:4][C:5](=[C:9]1[NH:14][CH2:13][CH2:12][CH2:11][S:10]1)[N+:6]([O-:8])=[O:7])[CH3:2].CC(C)=[O:17].I([O-])(=O)(=O)=O.[Na+].C(Cl)Cl>O>[CH2:1]([S:3]([CH2:4][C:5](=[C:9]1[NH:14][CH2:13][CH2:12][CH2:11][S:10]1)[N+:6]([O-:8])=[O:7])=[O:17])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6344DichloromethaneHCID 23667635Sodium periodateHCID 70251284HCID 70251284, compound

Product 1

HCID 68118329HCID 68118329, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2.34 g of 25 and 10 ml of acetone was added all at once to a solution of 2.25 g of sodium periodate in 15 ml of water. The resulting exothermic reaction was controlled between 25° and 35° by cooling. The mixture then as stirred at room temperature for 90 minutes, then was poured into a mixture of water and methylene chloride. The separated organic phase was washed with saturated sodium thiosulfate solution, and saturated sodium chloride. It then was dried (MgSO4) and the solvent evaporated under reduced pressure to give an oil, which was triturated with ether to give a yellow solid. This was chromatographed by a preparative thin layer chromatographic technique, on silica gel and using a mixture of methanol (2%) in methylene chloride as eluent, to give 26, as a yellow solid, m.p.: 102°-104°.

Workup

  1. customThe resulting exothermic reaction
  2. customwas controlled between 25° and 35°
  3. temperatureby cooling
  4. washThe separated organic phase was washed with saturated sodium thiosulfate solution, and saturated sodium chloride
  5. dry with materialIt then was dried (MgSO4)
  6. customthe solvent evaporated under reduced pressure
  7. customto give an oil, which
  8. customwas triturated with ether
  9. customto give a yellow solid
  10. customThis was chromatographed by a preparative thin layer chromatographic technique, on silica gel
  11. additiona mixture of methanol (2%) in methylene chloride as eluent

Sources & evidence

ORD record
ord-573c909733504febaa01bb2ed6572562
Source dataset
uspto-grants-1976_11
Patent number
US03993648

Reaction notes

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