Sodium Sulfite → HCID 86749318, compound

HRID 1439956Notes

Reaction equation

HRID 1439956 reaction equation
CC([C:4]1[C:12]2[O:11][C@@H:10]3[CH2:13][C@H:14]([OH:26])[C@@H:15]([NH:16][S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[C@@H:9]3[C:8]=2[CH:7]=[CH:6][CH:5]=1)=O.C(=O)([O-])O.[Na+].ClC1C=CC=[C:35]([C:39]([O:41]O)=[O:40])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:39]([O:41][C:4]1[C:12]2[O:11][C@@H:10]3[CH2:13][C@H:14]([OH:26])[C@@H:15]([NH:16][S:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)(=[O:18])=[O:19])[C@@H:9]3[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:40])[CH3:35]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86749319HCID 86749319, compound

Product 1

HCID 86749318HCID 86749318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1S, 2S, 3aR, 8bS)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl methyl ketone (112) (1.57 g) was dissolved in methylene chloride (30 ml) followed by the addition of sodium hydrogencarbonate (2.12 g) and metachloroperbenzoic acid (potency: 70%, 4.61) and stirring for 5 hours at room temperature. A 4% aqueous solution of sodium sulfite (100 ml) was added to the reaction mixture followed by extraction with methylene chloride (100 ml+50 ml×2). The organic layer was washed with saturated brine (50 ml×2) and concentrated to a solid after drying with anhydrous magnesium sulfate. The residue was purified with column chromatography (silica gel: n-hexane/ethyl acetate 1:1-1:2) to obtain (1S, 2S, 3aR, 8bS)-1-benzenesulfonamido-2-hydroxy- 2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl acetate (1.26 g).

Workup

  1. extractionfollowed by extraction with methylene chloride (100 ml+50 ml×2)
  2. washThe organic layer was washed with saturated brine (50 ml×2)
  3. concentrationconcentrated to a solid
  4. dry with materialafter drying with anhydrous magnesium sulfate
  5. customThe residue was purified with column chromatography (silica gel: n-hexane/ethyl acetate 1:1-1:2)

Sources & evidence

ORD record
ord-d3c4c32fdcfa43ef853a085ce9f3680c
Source dataset
uspto-grants-1996_03
Patent number
US05496849

Reaction notes

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