Methanol → HCID 70173611, compound

HRID 2186382Notes

Reaction equation

HRID 2186382 reaction equation
[O:1]=[C:2]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][C@@H:6]1[CH2:18]C(O)=O.S(=O)(=O)(O)O.[C:39](=[O:42])([O-])[OH:40].[Na+].[CH3:44]O>O>[O:1]=[C:2]([C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1)[CH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][NH:8][CH2:7][C@@H:6]1[CH2:18][C:39]([O:40][CH3:44])=[O:42]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 70176189(3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid

Product 1

HCID 70173611HCID 70173611, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 10.8 g of (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-3-acetic acid in 460 cm3 of anhydrous methanol to which 4.3 cm3 of concentrated sulfuric acid (d =1.83) had been added was heated at a temperature in the region of 65° C. with stirring for 2 hours. After cooling to approximately 20° 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 200 cm3 of water and rendered alkaline by addition of sodium hydrogencarbonate until a pH in the region of 8-9 was obtained. The mixture was extracted with 4 times 200 cm3 of ethyl acetate. The aqueous phase was basified to a pH in the region of 11 by addition of the necessary amount of sodium carbonate. The mixture was extracted with 2 times 200 cm3 of ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 6.84 g of methyl (3R,4R)-4-[3-oxo-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-acetate were obtained in the form of an oil with a brown color.

Workup

  1. temperatureAfter cooling to approximately 20° C.
  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. customwas obtained
  5. extractionThe mixture was extracted with 4 times 200 cm3 of ethyl acetate
  6. additionThe aqueous phase was basified to a pH in the region of 11 by addition of the necessary amount of sodium carbonate
  7. extractionThe mixture was extracted with 2 times 200 cm3 of ethyl acetate
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-63f6a28331bb438a8de950b12d3a1420
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

Loading…