HCID 12112580, compound → HCID 12112584, compound

HRID 1357053Notes

Reaction equation

HRID 1357053 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[O:18][CH2:17][O:16]3)=[N:10][C:9]=1[CH2:22][C:23]1[O:27][C:26](/[CH:28]=[CH:29]/[CH2:30][S:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:25][CH:24]=1>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[O:18][CH2:17][O:16]3)=[N:10][C:9]=1[CH2:22][C:23]1[O:27][C:26](/[CH:28]=[CH:29]/[CH2:30][S:31]([CH2:32][C:33]([OH:35])=[O:34])=[O:1])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 12112580HCID 12112580, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 12112584HCID 12112584, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A aqueous solution (100 ml) of OXONE (trade mark) (891 mg) was added dropwise to a solution of the compound prepared in Example 3(2) (1.0 g) in tetrahydrofuran (200 ml) over a period of 30 minutes at −2˜−3° C., and the resultant solution was stirred for 10 minutes at 0° C. Ice water was added to the reaction solution, and the resultant solution was extracted with ethyl acetate, and the extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (chloroform:methanol=50:1→10:1) to give the title compound (750 mg) having the following physical data.

Workup

  1. extractionthe resultant solution was extracted with ethyl acetate
  2. washthe extract was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=50:1→10:1)

Sources & evidence

ORD record
ord-d049c14fab0a4ed78dcada5ce93d1660
Source dataset
uspto-grants-2003_07
Patent number
US06589969B1

Reaction notes

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