Sodium Sulfite → HCID 86663883, compound

HRID 1022825Notes

Reaction equation

HRID 1022825 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH2:16][OH:17])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:15]([CH:16]=[O:17])[O:14][CH2:13][CH2:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 66976480HCID 66976480, compound

Product 1

HCID 86663883HCID 86663883, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-(hydroxymethyl)-1,4-oxazepane-4-carboxylate (3.0 g) in acetonitrile (20 mL) was added Dess-Martin reagent (5.1 g), and the mixture was stirred at 10° C. for 4 hr. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate and aqueous sodium sulfite solution, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated, under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-946805e4c5ee4b0482e814989419a28b
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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