Hydrochloric Acid → HCID 67067115, compound

HRID 2074333Notes

Reaction equation

HRID 2074333 reaction equation
[OH-].[Na+].[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[F:9][C:10]1[CH:11]=[C:12]([CH:48]=[CH:49][CH:50]=1)[CH2:13][O:14][C:15]1[CH:47]=[CH:46][C:18]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]3[CH:30]=[N:31][CH:32]=[C:33]([N:35]4[CH2:40][CH2:39][CH:38]([C:41]([O:43]CC)=[O:42])[CH2:37][CH2:36]4)[CH:34]=3)=[O:27])[CH2:22][CH2:21]2)=[CH:17][CH:16]=1.Cl>C1COCC1>[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[F:9][C:10]1[CH:11]=[C:12]([CH:48]=[CH:49][CH:50]=1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]3[CH:34]=[C:33]([N:35]4[CH2:40][CH2:39][CH:38]([C:41]([OH:43])=[O:42])[CH2:37][CH2:36]4)[CH:32]=[N:31][CH:30]=3)=[O:27])[CH2:22][CH2:21]2)=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67067075HCID 67067075, compound

Product 1

HCID 67067115HCID 67067115, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

An aqueous 1 M sodium hydroxide solution (3.24 ml) was added to a THF (10 ml) solution containing 5-[4-(ethoxycarbonyl)piperidin-1-yl]pyridin-3-yl 4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidine-1-carboxylate oxalate (240 mg), followed by stirring at 60° C. for 5 hours. 1 M hydrochloric acid (3.24 ml) was added to the reaction solution and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v)). The resulting oil was dissolved in ethanol/water, then oxalic acid (24 mg) was added thereto for crystallization to obtain 1-(5-{[(4-{4-[(3-fluorobenzyl)oxy]phenoxy}piperidin-1-yl)carbonyl]oxy}pyridin-3-yl)piperidine-4-carboxylic acid oxalate (93 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v))
  3. dissolutionThe resulting oil was dissolved in ethanol/water
  4. additionoxalic acid (24 mg) was added
  5. customfor crystallization

Sources & evidence

ORD record
ord-5c09302c6d8d41deb2caf35ee74a3822
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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