Sodium Hydroxide → HCID 11363729, compound

HRID 1767132Notes

Reaction equation

HRID 1767132 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1/[CH:11]=[CH:12]/[CH2:13][N:14]1[CH2:18][CH2:17][C:16]([CH2:23][CH2:24][CH2:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=3)[N:29]=[CH:28][C:27]=2[F:38])([C:19]([O:21]C)=[O:20])[CH2:15]1>O1CCOCC1.C(#N)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1/[CH:11]=[CH:12]/[CH2:13][N:14]1[CH2:18][CH2:17][C:16]([CH2:23][CH2:24][CH2:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=3)[N:29]=[CH:28][C:27]=2[F:38])([C:19]([OH:21])=[O:20])[CH2:15]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12993199HCID 12993199, compound

Product 1

HCID 11363729HCID 11363729, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

14.2 cm3 of a 5 N aqueous sodium hydroxide solution are added at a temperature in the region of 20° C. to 1.25 g (2.336 mmol) of methyl (±)-1-[(2E)-3-(2,5-difluorophenyl)-2-propenyl]-3-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-3-pyrrolidinecarboxylate in solution in 25 cm3 of dioxane. After stirring under reflux for 16 hours, the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 40 cm3 of acetonitrile. After stirring for 0.5 hour at a temperature in the region of 0° C., the orange solid in suspension is filtered, rinsed with twice 7 cm3 of acetonitrile and then dissolved in 55 cm3 of water. The aqueous phase is then acidified with 1 N hydrochloric acid to a pH value in the region of 6–7 and then extracted with twice 20 cm3 of dichloromethane. The organic phases are combined, washed with twice 10 cm3 of water, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 0.55 g of (±)-1-[(2E)-3-(2,5-difluorophenyl)-2-propenyl]-3-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-3-pyrrolidinecarboxylic acid, in the form of a yellow solid melting at 77° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. stirringAfter stirring for 0.5 hour at a temperature in the region of 0° C.
  5. filtrationthe orange solid in suspension is filtered
  6. washrinsed with twice 7 cm3 of acetonitrile
  7. dissolutiondissolved in 55 cm3 of water
  8. extractionextracted with twice 20 cm3 of dichloromethane
  9. washwashed with twice 10 cm3 of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-5bc01deab963450d8924a2d86324337e
Source dataset
uspto-grants-2007_06
Patent number
US07232833B2

Reaction notes

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