Sodium Sulfite → HCID 86663882, compound

HRID 1022823Notes

Reaction equation

HRID 1022823 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 66975211HCID 66975211, compound

Product 1

HCID 86663882HCID 86663882, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of tert-butyl (6S,7R)-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 (1.3 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-266928dcbc2f47a0b1146edaac9b8d2e
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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