1,4-Dioxane → HCID 68992721, compound

HRID 1725935Notes

Reaction equation

HRID 1725935 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:17]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:16]([CH3:28])[C:15]([CH:29]=[CH2:30])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:31]1CCOCC1>O.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:17]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])=[C:16]([CH3:28])[C:15]([CH:29]([OH:31])[CH3:30])=[CH:14][CH:13]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 68864019HCID 68864019, compound

Product 1

HCID 68992721HCID 68992721, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Example 173B (150 mg, 0.35 mmol) in dioxane (6 mL) and water (2 mL) was added OSO4 (2.5% wt in t-butanol, 0.5 mL) was stirred for 8 minutes at ambient temperature, treated with NaIO4 (128 mg, 0.6 mmol), stirred for 30 minutes, treated with brine, and extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated. The concentrate was dissolved in anhydrous THF (6 mL), cooled to 0° C., treated dropwise with methyl magnesium bromide (3.0M in diethyl ether, 0.37 mL), treated with water (20 mL) and 1N HCl (1.0 mL), and extracted with ethyl acetate (2×20 mL). The ethyl acetate solution was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography on silica gel with 40% ethyl acetate/hexanes to provide the desired product.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in anhydrous THF (6 mL)
  7. temperaturecooled to 0° C.
  8. additiontreated dropwise with methyl magnesium bromide (3.0M in diethyl ether, 0.37 mL)
  9. additiontreated with water (20 mL) and 1N HCl (1.0 mL)
  10. extractionextracted with ethyl acetate (2×20 mL)
  11. dry with materialThe ethyl acetate solution was dried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was purified by flash column chromatography on silica gel with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-024fe227498f4c57845c8a3bb6e082c3
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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