Hydrochloric Acid → HCID 131722262, compound

HRID 565617Notes

Reaction equation

HRID 565617 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[C@@H:14]1[C@H:19]2[CH2:20][C@@:16]([N:21]=[S:22](=[O:24])=[O:23])([CH2:17][CH2:18]2)[C@@H:15]1[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32].[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[C@@H:14]1[C@H:19]2[CH2:20][C@@:16]([N:21]=[S:22](=[O:24])=[O:23])([CH2:17][CH2:18]2)[C@@H:15]1[CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 131722263HCID 131722263, compound

Product 1

HCID 131722262HCID 131722262, compoundYield 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-89b026771d6b4f2e89e44c3c442409ab
Source dataset
uspto-grants-2001_01
Patent number
US06172113B2

Reaction notes

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