Hydrochloric Acid → (Z)-7-[(1S,2R,3R,4R)-3-(Dibenzofuran-2-sulfonylamino)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid

HRID 2300716Notes

Reaction equation

HRID 2300716 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:14]([NH:17][C@@H:18]1[C@H:23]2[CH2:24][C@H:20]([CH2:21][CH2:22]2)[C@H:19]1[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32])(=[O:16])=[O:15].[OH-].[K+].Cl>CO.O1CCCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:14]([NH:17][C@@H:18]1[C@H:23]2[CH2:24][C@H:20]([CH2:21][CH2:22]2)[C@H:19]1[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:15])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 131722261methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate

Product 1

HCID 10671942(Z)-7-[(1S,2R,3R,4R)-3-(Dibenzofuran-2-sulfonylamino)-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1a-1) (234 mg, 0.50 mmol) was dissolved in methanol (6 ml)/tetrahydrofuran (4 ml). To the solution was added 1 N potassium hydroxide (1.50 ml, 1.50 mmol) under ice-cooling. After the reaction mixture was warmed up to room temperature, it was allowed to react for 16 hr and concentrated to remove the solvent. To the residue were added ethyl acetate (50 ml) and water (10 ml), and then 1 N HCl (2.00 ml, 2.00 mmol), and the organic layer was separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:1) containing 0.2% acetic acid) to yield (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1a-2) (203 mg, 0.434 mmol). Yield 87%, oil.

Workup

  1. temperaturecooling
  2. customto react for 16 hr
  3. concentrationconcentrated
  4. customto remove the solvent
  5. additionTo the residue were added ethyl acetate (50 ml) and water (10 ml)
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:1) containing 0.2% acetic acid)

Sources & evidence

ORD record
ord-05eeea1d1a364335853cf793ddf53fcf
Source dataset
uspto-grants-2002_12
Patent number
US06498190B1

Reaction notes

Loading…