Citric Acid → HCID 69836777, compound

HRID 2186386Notes

Reaction equation

HRID 2186386 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C@@H:14]([CH2:17][CH2:18][CH:19]([OH:32])[C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)[C@@H:13]([CH2:33][C:34]([O:36]C)=[O:35])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O.CO.ClCCl.CO>[F:1][C:2]1[CH:3]=[C:4]([S:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C@@H:14]([CH2:17][CH2:18][CH:19]([OH:32])[C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)[C@@H:13]([CH2:33][C:34]([OH:36])=[O:35])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 131723285HCID 131723285, compound

Product 1

HCID 69836777HCID 69836777, compoundYield 86.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1.3 g of methyl (3R,4R)-1-[2-(3-fluorophenylthio)ethyl]-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-acetate in 20 cm3 of dioxane, to which 2 cm3 of 5N aqueous sodium hydroxide solution had been added, was heated with stirring for 20 hours at a temperature in the region of 60° C. The reaction mixture was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. and then the residue obtained was taken up in 30 cm3 of water and 5 cm3 of methanol, acidified with citric acid. The solvents were evaporated under the same conditions as above and then the residue obtained was taken up in 70 cm3 of a dichloromethane/methanol (80/20 by volume) mixture. The citric acid crystals were filtered off; the filtrate was evaporated as above and the evaporation residue was taken up in 30 cm3 of diethyl ether, filtered off, and dried in the air. 1.1 g of (3R,4R)-1-[2-(3-fluorophenylthio)ethyl]-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-acetic acid were obtained in the form of a solid with a cream color.

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  3. customthe residue obtained
  4. customThe solvents were evaporated under the same conditions as above and then the residue
  5. customobtained
  6. filtrationThe citric acid crystals were filtered off
  7. customthe filtrate was evaporated as above and the evaporation residue
  8. filtrationfiltered off
  9. customdried in the air

Sources & evidence

ORD record
ord-ec50db41f78742ff9750c0e3d340a2e3
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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