Hydrochloric Acid → HCID 69898926, compound

HRID 394704Notes

Reaction equation

HRID 394704 reaction equation
[OH:1][CH:2]([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[F:37])[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[CH2:19][C:20]([O:22]CC)=[O:21].[OH-].[Na+].[ClH:40]>O.ClCCl.CC(C)=O.O1CCOCC1>[ClH:40].[ClH:40].[OH:1][CH:2]([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[F:37])[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[CH2:19][C:20]([OH:22])=[O:21]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131724008HCID 131724008, compound

Product 1

HCID 69898926HCID 69898926, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 70 mg of ethyl (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-[2-(thien-2-ylthio)ethyl]piperidine-3-acetate, 1 cm3 of dioxane and 0.3 cm3 of a 1 N aqueous sodium hydroxide solution was heated, with stirring, at a temperature in the region of 60° C. for 1 hour. 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 25 cm3 of water and 10 cm3 of dichloromethane. The aqueous phase was separated after settling out and then acidified by pouring 0.3 cm3 of 1 N hydrochloric acid. The precipitate formed was dissolved by adding 25 cm3 of dichloromethane. The organic phase was washed with 10 cm3 of a saturated aqueous sodium chloride solution and dried over magnesium sulfate, filtered and concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was then dissolved in the hot state in 2 cm3 of acetone. 0.07 cm3 of 4 N hydrochloric acid in dioxane were poured over this solution. The resulting mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 72 mg of (3RS,4RS)-4-[3-(R,S)-hydroxy-3-(3-fluoro-6-methoxy quinolin-4-yl)propyl]-1-[2-(thien-2-ylthio)ethyl]piperidine-3-acetic acid dihydrochloride were obtained in the form of a powder, which was white in color.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  2. customthe residue obtained
  3. customThe aqueous phase was separated
  4. additionby pouring 0.3 cm3 of 1 N hydrochloric acid
  5. customThe precipitate formed
  6. dissolutionwas dissolved
  7. washThe organic phase was washed with 10 cm3 of a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  11. customThe residue obtained
  12. concentrationThe resulting mixture was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-8ee28cbf82944054bf7465ea0c5e29d2
Source dataset
uspto-grants-2003_08
Patent number
US06602884B2

Reaction notes

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