Sodium Sulfite → HCID 86749315, compound

HRID 1439954Notes

Reaction equation

HRID 1439954 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 86749316HCID 86749316, compound

Product 1

HCID 86749315HCID 86749315, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R, 2R, 3aS, 8bR)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta [b]benzofuran-5-yl methyl ketone (111) (219 mg) was dissolved in methylene chloride (4 ml) followed by the addition of sodium hydrogencarbonate (197 mg, 2.3 mmol) and metachloroperbenzoic acid (potency: 70%, 289 mg) and stirring for 2 hours at room temperature. A 3% aqueous solution of sodium sulfite (15 ml) was added to the reaction mixture followed by extraction with methylene chloride (15 ml+10 ml×2). The organic layer was washed with water (15 ml) and saturated brine (15 ml) and concentrated after drying with anhydrous magnesium sulfate. The residue was purified with column chromatography (silica gel: cyclohexane/ethyl acetate 1:2) to obtain (1R, 2R, 3aS, 8bR)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl acetate (190 mg).

Workup

  1. extractionfollowed by extraction with methylene chloride (15 ml+10 ml×2)
  2. washThe organic layer was washed with water (15 ml) and saturated brine (15 ml)
  3. concentrationconcentrated
  4. dry with materialafter drying with anhydrous magnesium sulfate
  5. customThe residue was purified with column chromatography (silica gel: cyclohexane/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-c72c6c1813334885af9cf1c71fee950e
Source dataset
uspto-grants-1996_03
Patent number
US05496849

Reaction notes

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