Water → HCID 67075190, compound

HRID 38456Notes

Reaction equation

HRID 38456 reaction equation
C([O:3][C:4]([CH:6]1[CH2:13][CH:12]2[C:14](=[O:15])[CH:8]([CH2:9][S:10][CH2:11]2)[CH2:7]1)=[O:5])C.O.[OH-].[Na+]>C1COCC1>[O:15]=[C:14]1[CH:8]2[CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:13][CH:12]1[CH2:11][S:10][CH2:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67075308Ethyl 9-oxo-3-thiabicyclo[3.3.1]nonane-7-carboxylate

Product 1

HCID 67075190HCID 67075190, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9-oxo-3-thia-bicyclo[3.3.1]nonane-7-carboxylic acid ethyl ester (5 g, 22 mmol) in a THF (55 ml)/water (30 ml) mixture at 0° C. was added dropwise a 1N sodium hydroxide solution (24 ml, 24 mmol). The reaction mixture was stirred at room temperature overnight, then heated to 60° C. for 1 hour before THF was evaporated. The remaining aqueous layer was washed with ethyl acetate, acidified with 1N HCl, the resulting precipitate was filtered and dried to yield 9-oxo-3-thia-bicyclo[3.3.1]nonane-7-carboxylic acid (2.22 g) as a solid.

Workup

  1. customwas evaporated
  2. washThe remaining aqueous layer was washed with ethyl acetate
  3. filtrationthe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-56330cdb748644c693aff158559aae5d
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Reaction notes

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