Sodium Hydroxide → HCID 25128027, compound

HRID 2407482Notes

Reaction equation

HRID 2407482 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1([C:36]([O:38]CC)=[O:37])[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)[O:23][N:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])C>C(O)C.O1CCCC1>[F:34][C:32]([F:33])([F:35])[C:29]1[CH:30]=[CH:31][C:26]([C:24]2[O:23][N:22]=[C:21]([C:18]3[CH:17]=[CH:16][C:15]([CH2:14][N:11]4[CH2:10][CH2:9][C:8]([C:36]([OH:38])=[O:37])([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]4)=[CH:20][CH:19]=3)[N:25]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59509451HCID 59509451, compound

Product 1

HCID 25128027HCID 25128027, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution (10 mL) of sodium hydroxide (0.86 g, 0.0215 mol) is added to a stirred solution of 1-{4-[5-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid diethyl ester (2.3 g, 0.004 mol) in a mixture of ethanol (50 mL) and tetrahydrofuran (10 mL). The reaction mixture is refluxed for 20 hrs, then is concentrated under reduced pressure. The residue is acidified with 3N HCl to pH ˜2. The solid thus formed is filtered, washed with a mixture of methanol:ether (30 mL, 10:90), then tetrahydrofuran (20 mL) and dried to furnish 1-{4-[5-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-3-yl]benzyl}-piperidine-4,4-dicarboxylic acid (e.g. 14).

Workup

  1. temperatureThe reaction mixture is refluxed for 20 hrs
  2. concentrationis concentrated under reduced pressure
  3. customThe solid thus formed
  4. filtrationis filtered
  5. washwashed with a mixture of methanol
  6. dry with materialether (30 mL, 10:90), then tetrahydrofuran (20 mL) and dried

Sources & evidence

ORD record
ord-9e56d0f39f614b61a2af265454eb9331
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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