HCID 54196894, compound → HCID 86755973, compound

HRID 369875Notes

Reaction equation

HRID 369875 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]([OH:31])[CH2:24][P:25](=[O:30])([O:28][CH3:29])[O:26][CH3:27])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([NH:13][C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)=[O:12]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([NH:13][C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)=[O:12])[C:23]([CH2:24][P:25](=[O:30])([O:28][CH3:29])[O:26][CH3:27])=[O:31]

Participants

4

Reactant 1

HCID 54196894HCID 54196894, compound

Product 1

HCID 86755973HCID 86755973, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst3×HCID 6212ChloroformSolvent

Procedure

To a solution of dimethyl {2-[3-methoxy-4-(2-benzothiazolylaminocarbonylmethoxy)phenyl]-2-hydroxyethyl}phosphonate (19.0 g) in chloroform (300 ml) is added active manganese dioxide (17.7 g), and the mixture is refluxed for three hours. To the mixture is additionally added active manganese dioxide (18 g), and the mixture is refluxed for three hours. To the mixture is further added active manganese dioxide (20 g), and the mixture is refluxed for three hours. The manganese dioxide is collected by filtration, and washed with chloroform. The filtrate and the washings are combined and concentrated under reduced pressure to remove the chloroform. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=200:1→50:1) to give dimethyl {[3-methoxy-4-(2-benzothiazolylaminocarbonylmethoxy)benzoyl]methyl}phosphonate (7.76 g).

Workup

  1. temperaturethe mixture is refluxed for three hours
  2. temperaturethe mixture is refluxed for three hours
  3. temperaturethe mixture is refluxed for three hours
  4. filtrationThe manganese dioxide is collected by filtration
  5. washwashed with chloroform
  6. concentrationconcentrated under reduced pressure
  7. customto remove the chloroform
  8. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=200:1→50:1)

Sources & evidence

ORD record
ord-e30c122c5e6d485dab4144292fc40757
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

Loading…