1,4-Dioxane → HCID 68864277, compound

HRID 1725933Notes

Reaction equation

HRID 1725933 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]=C)=[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:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:16]([CH3:28])[C:15]([CH2:29][OH:31])=[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 68864277HCID 68864277, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Example 173B (127 mg, 0.3 mmol) in dioxane (6 mL) and water (2 mL) was treated with OSO4 (2.5% wt in t-butanol, 0.5 mL), stirred for 8 minutes at ambient temperature, treated with NaIO4 (128 mg, 0.6 mmol), stirred for 30 minutes, diluted with brine, and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4), filtered, and concentrated. This concentrate was dissolved in absolute ethanol (5 mL) and THF (5 mL), treated with NaBH4 (7 mg), stirred for 30 minutes, treated with brine (10 mL), and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4), filtered and concentrated. The residue was purified by flash column chromatography with 45% ethyl acetate/hexanes to provide the desired product (71 mg, 56.7%). 1H NMR (DMSO-d6) δ 2.05 (s, 3H), 4.42 (d, 2H), 5.12 (t, 1H), 5.24 (s, 2H), 6.84 (d, 1H), 7.35-7.46 (m, 8H), 7.70-7.75 (m, 2H), 9.81 (s, 1H); MS (ESI(−)) m/e 428 (M−H)−.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThis concentrate was dissolved in absolute ethanol (5 mL)
  7. additionTHF (5 mL), treated with NaBH4 (7 mg)
  8. stirringstirred for 30 minutes
  9. additiontreated with brine (10 mL)
  10. extractionextracted with ethyl acetate
  11. dry with materialThe ethyl acetate solution was dried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customThe residue was purified by flash column chromatography with 45% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d19c0940e05844c89b2217699b0ece2f
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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