Chloroform → HCID 69837520, compound

HRID 2186398Notes

Reaction equation

HRID 2186398 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][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:9][C@@H:8]1[CH2:21][C:22]([O:24]C)=[O:23].[OH-].[Na+].C(Cl)(Cl)Cl>O1CCOCC1.C(OCC)C>[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][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:9][C@@H:8]1[CH2:21][C:22]([OH:24])=[O:23]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 131723291HCID 131723291, compound

Product 1

HCID 69837520HCID 69837520, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1.6 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-acetate dihydrochloride in 30 cm3 of dioxane, to which had been added 2.6 cm3 of 5N aqueous sodium hydroxide solution, was stirred for 6 hours at a temperature in the region of 65° C. After concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C., a residue was obtained, which residue was taken up in 2 times 30 cm3 of chloroform and which was concentrated as under the above conditions. The residue was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 3 cm; silica volume 100 cm3), elution was carried out with a chloroform/methanol/28% aqueous ammonia (12/3/0.5 by volume) mixture, and 30-cm3 fractions were collected. The fractions comprising the expected product were combined and concentrated as above. 1.5 g of a colorless lacquer were obtained, which product was taken up in 20 cm3 of diethyl ether, filtered, and washed with 2 times 10 cm3 of diethyl ether. The product was dried under partial pressure (5 kPa) and then to constant weight in an oven under reduced pressure (10 Pa) at a temperature in the region of 40° C. 1.35 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(cyclopentylthio)ethyl]piperidine-3-acetic acid were obtained in the form of a white solid.

Workup

  1. concentrationAfter concentrating the reaction mixture under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  2. customa residue was obtained
  3. concentrationwas concentrated as under the above conditions
  4. customThe residue was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm; diameter 3 cm; silica volume 100 cm3), elution
  5. customwere collected
  6. concentrationconcentrated as above
  7. custom1.5 g of a colorless lacquer were obtained
  8. filtrationfiltered
  9. washwashed with 2 times 10 cm3 of diethyl ether
  10. customThe product was dried under partial pressure (5 kPa)
  11. customin the region of 40° C

Sources & evidence

ORD record
ord-1053f858e5b24d64ae856ed99005cda9
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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