Acetic Acid → HCID 69837074, compound

HRID 2186341Notes

Reaction equation

HRID 2186341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][C@@H:17]1[C:31]([O:33]C)=[O:32].[OH-].[Na+].C(O)(=O)C>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][CH2:15][C@@H:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][S:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:18][C@@H:17]1[C:31]([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86758143HCID 86758143, compound

Product 1

HCID 69837074HCID 69837074, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
80 °C

Procedure

A suspension of 0.7 g of methyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(phenylthio)ethyl]piperidine-3-carboxylate in 5 cm3 of methanol, to which methanol had been added 2.9 Cm3 of N aqueous sodium hydroxide, was stirred for 2 hours at a temperature in the region of 80° C. The solution obtained was neutralized with 0.18 cm3 of acetic acid and then evaporated 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 40-63 μm; diameter 3 cm; height 20 cm), elution was carried out with a dichloromethane/ethanol (90/10 by volume) mixture, and 20-cm3 fractions were collected. Fractions 21 to 52 were region of 40° C. 0.53 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(phenylthio)ethyl]piperidine-3-carboxylic acid was obtained in the form of an oil with a beige color.

Workup

  1. customThe solution obtained
  2. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  3. customThe residue obtained
  4. customwas purified by chromatography at atmospheric pressure on a column of silica gel (particle size 40-63 μm; diameter 3 cm; height 20 cm), elution
  5. customwere collected
  6. customregion of 40° C

Sources & evidence

ORD record
ord-1e645b08fcc74043be55c001ca7f9683
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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