Sodium Hydroxide → HCID 69353351, compound

HRID 2186350Notes

Reaction equation

HRID 2186350 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[CH2:15][CH2:16][CH2:17][C@@H:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]#[C:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH2:20][C@@H:19]1[C:32]([O:34]C)=[O:33]>O1CCOCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[CH2:15][CH2:16][CH2:17][C@@H:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]#[C:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH2:20][C@@H:19]1[C:32]([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86758154HCID 86758154, compound

Product 1

HCID 69353351HCID 69353351, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

3.9 cm3 of 1N aqueous sodium hydroxide were added to a solution of 0.6 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2ynyl]piperidine-3-carboxylate in 10 cm3 of dioxane and then the mixture was heated at a temperature in the region of 65° C. for 16 hours. The mixture was cooled and then the organic phase was extracted with 3 times 50 cm3 of ethyl acetate. The aqueous phase was acidified with 3.9 cm3 of 1N hydrochloric acid. The solution was taken up in 10 cm3 of a saturated aqueous sodium bicarbonate solution and then the organic phase was extracted with 2 times 20 cm3 of ethyl acetate and 2 times 20 cm3 of dichloromethane, dried over sodium sulfate, filtered, and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 45° C. 0.32 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-(thien-3-yl)prop-2-ynyl]piperidine-3-carboxylic acid was obtained in the form of a foam with a white color.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe organic phase was extracted with 3 times 50 cm3 of ethyl acetate
  3. extractionthe organic phase was extracted with 2 times 20 cm3 of ethyl acetate and 2 times 20 cm3 of dichloromethane
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 45° C

Sources & evidence

ORD record
ord-63504731d187438a938d7bfdd0d9d65c
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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