Hydrochloric Acid → (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride

HRID 2186365Notes

Reaction equation

HRID 2186365 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][CH:26]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:9][C@@H:8]1[C:21]([O:23]C)=[O:22].[ClH:37].[Cl:38]CCl.CO>CO.O>[ClH:38].[ClH:37].[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][CH:26]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:9][C@@H:8]1[C:21]([OH:23])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 131723277methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)-ethyl]piperidine-3-carboxylate

Product 1

HCID 70175549(3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2 cm3 of 5N aqueous sodium hydroxide solution were added, with stirring and under an inert atmosphere, to a solution of 0.48 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-carboxylate in 10 cm3 of methanol. After heating the mixture for 16 hours at a temperature in the region of 60° C., the reaction mass was evaporated under reduced pressure (2.9 kPa) at a temperature in the region of 60° C. and the residue obtained was taken up in 4.3 cm3 of distilled water to which had been added 4.3 cm3 of 28% hydrochloric acid. The remaining insoluble material was filtered off and then the filtrate was evaporated under the same conditions as above. The residue obtained was stirred in a dichloromethane/methanol (90/10 by volume) mixture. The resulting precipitate was filtered off and washed with 3 times 2.5 cm3 of the same mixture. The filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 0.48 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride was obtained in the form of a foam with a green color melting with softening at a temperature in the region of 156° C.

Workup

  1. customthe reaction mass was evaporated under reduced pressure (2.9 kPa) at a temperature in the region of 60° C.
  2. customthe residue obtained
  3. filtrationThe remaining insoluble material was filtered off
  4. customthe filtrate was evaporated under the same conditions as above
  5. customThe residue obtained
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with 3 times 2.5 cm3 of the same mixture
  8. customThe filtrate was evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-5d2b29280ee945ee876ec3f83db340a0
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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