Sodium Hydroxide → HCID 22643893, compound

HRID 394715Notes

Reaction equation

HRID 394715 reaction equation
[OH:1][CH:2]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][C:24]=1[F:35])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH:6]1[C:19]([O:21]C)=[O:20].O1CCOCC1.[OH-].[Na+]>O.C(OCC)C>[OH:1][CH:2]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=2)[N:26]=[CH:25][C:24]=1[F:35])[CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][S:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][CH:6]1[C:19]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 312751,4-DioxaneHCID 131724014HCID 131724014, compound

Product 1

HCID 22643893HCID 22643893, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 630 mg of methyl (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-carboxylate, 6-cm3 of dioxane and 3-cm3 of a 1 N aqueous sodium hydroxide solution was heated with stirring at a temperature in the region of 60° C. for 2 hours. 3-cm3 of a 1 N aqueous sodium hydroxide solution were added and the solution was heated for 1 hour at 60° C. After concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C., the residue obtained was taken up in 20-cm3 of water and 20-cm3 of diethyl ether. The aqueous phase was separated after settling out and was then acidified by pouring in 6-cm3 of 1 N hydrochloric acid. The white precipitate formed was extracted with 150-cm3 of ethyl acetate. The organic phase was washed twice with 10-cm3 of a saturated aqueous sodium chloride solution and dried over magnesium sulfate, filtered, and then concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 499 mg of (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-carboxylic acid were obtained in the form of a white solid.

Workup

  1. temperaturethe solution was heated for 1 hour at 60° C
  2. concentrationAfter concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  3. customthe residue obtained
  4. customThe aqueous phase was separated
  5. additionby pouring in 6-cm3 of 1 N hydrochloric acid
  6. customThe white precipitate formed
  7. extractionwas extracted with 150-cm3 of ethyl acetate
  8. washThe organic phase was washed twice with 10-cm3 of a saturated aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-bd3f253d2fc84d68bfcb50f5d0da79e1
Source dataset
uspto-grants-2003_08
Patent number
US06602884B2

Reaction notes

Loading…