Sodium Hydroxide → HCID 10459358, compound

HRID 1760229Notes

Reaction equation

HRID 1760229 reaction equation
[OH-].[Na+].[OH:3][CH:4]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[N:28]=[CH:27][C:26]=1[Cl:37])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:9][CH:8]1[C:21]([O:23]C)=[O:22]>O1CCOCC1>[OH:3][CH:4]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=2)[N:28]=[CH:27][C:26]=1[Cl:37])[CH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:9][CH:8]1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12114749HCID 12114749, compound

Product 1

HCID 10459358HCID 10459358, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

2.7 cm3 of a 1 N aqueous sodium hydroxide solution are added to 480 mg of methyl 4-[3-hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylsulfanyl)ethyl]piperidine-3-carboxylate (ester isomer A) solubilized in 10 cm3 of dioxane. The reaction medium is then heated at 70° C. for 5 h 30 min. The temperature is then allowed to return to 19° C. for 12 hours. Evaporation is carried out under reduced pressure (20 kPa; 45° C.). The residue is taken up in 25 cm3 of distilled water and then extraction is carried out with 25 cm3 of diethyl ether. The aqueous phase is acidified with 2.6 cm3 of a 1 N aqueous hydrochloric acid solution (pH=6) and then this phase is extracted with 3 times 70 cm3 of ethyl acetate. The organic phase is dried under magnesium sulfate, filtered through a sintered glass funnel, and then evaporated under reduced pressure (20 kPa; 45° C.). After having dried under vacuum (50 kPa) for 4 hours, 360 mg of 4-[3-hydroxy-3-(3-chloro-6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylsulfanyl)ethyl]piperidine-3-carboxylic acid, in the form of a pale yellow solid (isomer A), are obtained.

Workup

  1. customEvaporation
  2. customis carried out under reduced pressure (20 kPa; 45° C.)
  3. extractionextraction
  4. extractionthis phase is extracted with 3 times 70 cm3 of ethyl acetate
  5. customThe organic phase is dried under magnesium sulfate
  6. filtrationfiltered through a sintered glass funnel
  7. customevaporated under reduced pressure (20 kPa; 45° C.)
  8. customAfter having dried under vacuum (50 kPa) for 4 hours

Sources & evidence

ORD record
ord-7e4c6f08980a412db0d1b7a3e345cb2c
Source dataset
uspto-grants-2005_01
Patent number
US06841562B2

Reaction notes

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