Sodium Hydroxide → HCID 9827322, compound

HRID 2186380Notes

Reaction equation

HRID 2186380 reaction equation
Cl.Cl.[OH:3][CH:4]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][CH:27]=1)[CH2:5][CH2:6][C@@H: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][C@@H:8]1[CH2:21][C:22]([O:24]C)=[O:23].[OH-].[Na+]>O1CCOCC1>[OH:3][CH:4]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][CH:27]=1)[CH2:5][CH2:6][C@@H: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][C@@H:8]1[CH2:21][C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131723282HCID 131723282, compound

Product 1

HCID 9827322HCID 9827322, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.22 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(2-thienylthio)ethyl]piperidine-3-acetate dihydrochloride in 5 cm3 of dioxane, to which had been added 0.683 cm3 of 5N aqueous sodium hydroxide solution, was stirred for 20 hours at a temperature in the region of 60° C. After evaporating under reduced pressure (5 kPa) at a temperature in the region of 40 ° C., the residue obtained was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μ; diameter 1 cm; silica volume 20 cm3), elution was carried out with a chloroform/methanol/aqueous ammonia (12/3/1 by volume) mixture. Fractions 1 to 3 were combined and concentrated under the above conditions. A product was obtained, which product was dried in an oven to constant weight under reduced pressure (10 Pa) at a temperature in the region of 40° C. 0.179 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin4-yl)propyl]-1-[2-(2-thienylthio)-ethyl]piperidine-3-acetic acid was obtained in the form of a white foam which was a mixture of two diastereoisomers.

Workup

  1. customAfter evaporating under reduced pressure (5 kPa) at a temperature in the region of 40 ° C.
  2. customthe residue obtained
  3. customwas purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μ; diameter 1 cm; silica volume 20 cm3), elution
  4. concentrationconcentrated under the above conditions
  5. customA product was obtained
  6. customwhich product was dried in an oven to constant weight under reduced pressure (10 Pa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-fa82b39c48d44a759d6e02df7b98b031
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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