Sodium Hydroxide → HCID 59398414, compound

HRID 39799Notes

Reaction equation

HRID 39799 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][C:15]([CH2:23][CH2:24][CH2:25][N:26]4[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=5)[CH:29]=[CH:28][C:27]4=[O:38])([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][N:12]3[CH2:13][CH2:14][C:15]([CH2:23][CH2:24][CH2:25][N:26]4[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=5)[CH:29]=[CH:28][C:27]4=[O:38])([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59397828ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 59398414HCID 59398414, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1 mL of an ethanol solution containing 0.10 g of ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylate, 0.15 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 2 hours. Then, more 0.10 mL of 20% aqueous sodium hydroxide solution was added and refluxed with heating for 5 hours. After left to stand at room temperature overnight, the solvent was removed under reduced pressure, water was added, and adjusted to pH 6.7 with 6.0 mol/L hydrochloric acid. The solvent was removed under reduced pressure, and the residue thus obtained was purified by reversed-phase silica gel column chromatography [eluent; acetonitrile: water=3: 7] to give 21 mg of 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(3-(7-methoxy-2-oxoquinolin-1(2H)-yl)propyl)piperidine-4-carboxylic acid as a white solid.

Workup

  1. additionwas added
  2. temperaturerefluxed
  3. temperaturewith heating for 2 hours
  4. temperaturerefluxed
  5. temperaturewith heating for 5 hours
  6. waitAfter left
  7. customthe solvent was removed under reduced pressure, water
  8. additionwas added
  9. customThe solvent was removed under reduced pressure
  10. customthe residue thus obtained
  11. customwas purified by reversed-phase silica gel column chromatography [eluent; acetonitrile: water=3: 7]

Sources & evidence

ORD record
ord-a8493697af894fe89af4b1b586e2a126
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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