Hydrochloric Acid → HCID 68629411, compound

HRID 2070603Notes

Reaction equation

HRID 2070603 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([O:13][CH2:14][CH:15]2[CH2:24][CH2:23][CH2:22][C:17]3([CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:16]2)=[CH:11][CH:12]=1)C.O1CCCC1.[OH-].[Na+].[ClH:33]>C(O)C>[ClH:33].[CH2:18]1[C:17]2([CH2:22][CH2:23][CH2:24][CH:15]([CH2:14][O:13][C:10]3[N:9]=[CH:8][C:7]([CH2:6][CH2:5][C:4]([OH:25])=[O:3])=[CH:12][CH:11]=3)[CH2:16]2)[CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57771413HCID 57771413, compound

Product 1

HCID 68629411HCID 68629411, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[6-(spiro[4.5]dec-7-ylmethoxy)-pyridin-3-yl]-propionic acid ethyl ester (36 mg) obtained in Step 3 in a mixed solvent of tetrahydrofuran (0.36 mL)-ethanol (0.36 mL) was added 1N aqueous sodium hydroxide solution (0.21 mL), followed by stirring the reaction mixture at room temperature for 1.5 hours. Then, to the reaction mixture was added 1N aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was dissolved in a 1,4-dioxane solution of hydrogen chloride (4M, 0.5 mL), and to this was added hexane (0.5 mL) while stirring. The resulting solid was filtered and then dried to give 3-[6-(spiro[4.5]dec-7-ylmethoxy)-pyridin-3-yl]-propionic acid hydrochloride (33 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in a 1,4-dioxane solution of hydrogen chloride (4M, 0.5 mL)
  6. additionto this was added hexane (0.5 mL)
  7. stirringwhile stirring
  8. filtrationThe resulting solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-c38bc508816a4940aeebed8c828c5554
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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