Sodium Hydroxide → (3r,4r)-1-[2-(Thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid

HRID 393221Notes

Reaction equation

HRID 393221 reaction equation
[OH-].[Na+].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[S:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C@@H:14]([CH2:17][CH2:18][CH:19]([NH2:32])[C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)[C@@H:13]([C:33]([O:35]C)=[O:34])[CH2:12]1>O1CCOCC1.CO.O>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[S:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C@@H:14]([CH2:17][CH2:18][CH:19]([NH2:32])[C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][CH:21]=2)[C@@H:13]([C:33]([OH:35])=[O:34])[CH2:12]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 131724623Methyl (3r,4r)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

Product 1

HCID 69855381(3r,4r)-1-[2-(Thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acidYield 102.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1 cm3 of 5N aqueous sodium hydroxide solution is added with stirring, at a temperature in the region of 20° C., to a solution of 0.05 g of methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 2 cm3 of dioxane and 2 cm3 of methanol, and then the combined mixture is brought to reflux and refluxed for 20 hours. The mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is dissolved in 6 cm3 of distilled water The aqueous phase is washed with 2 cm3 of methylene chloride and then evaporated to dryness. The residue is taken up in 2 cm3 of isopropanol and the insoluble material is washed with 2 cm3 of isopropanol and then dried to give 0.05 g of (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid, sodium salt.

Workup

  1. temperatureto reflux
  2. temperaturerefluxed for 20 hours
  3. concentrationThe mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  4. customThe residue obtained
  5. washis washed with 2 cm3 of methylene chloride
  6. customevaporated to dryness
  7. washthe insoluble material is washed with 2 cm3 of isopropanol
  8. customdried

Sources & evidence

ORD record
ord-38b6889654ba4f3181315d226aa4775e
Source dataset
uspto-grants-2004_10
Patent number
US06806277B2

Reaction notes

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