Sodium Hydroxide → 1-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester

HRID 2407486Notes

Reaction equation

HRID 2407486 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([C:13]1([C:44]([O:46]CC2C=CC=CC=2)=[O:45])[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[N:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)=[C:33]([F:43])[CH:32]=4)[O:28][N:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[CH2:3]([O:10][C:11]([C:13]1([C:44]([OH:46])=[O:45])[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[N:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)=[C:33]([F:43])[CH:32]=4)[O:28][N:27]=3)=[CH:24][CH:25]=2)[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 595094331-{4-[5-(2-Fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}piperidine-4,4-dicarboxylic acid dibenzyl ester

Product 1

HCID 595094311-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution (50 mL) of sodium hydroxide (1.7 g, 0.043 mol) is added to a stirred solution of 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}piperidine-4,4-dicarboxylic acid dibenzyl ester (18.3 g, 0.027 mol) in tetrahydrofuran (150 mL). The reaction mixture is stirred overnight at room temperature and then concentrated under reduced pressure. The residue is acidified to pH ˜6 with diluted hydrochloric acid to give a solid which is filtered and washed with diethylether (100 mL) to furnish 1-{4-[5-(2-fluorobiphenyl-4-yl)-1,2,4-oxadiazole-3-yl]benzyl}piperidine-4,4-dicarboxylic acid mono benzyl ester.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a solid which
  3. filtrationis filtered
  4. washwashed with diethylether (100 mL)

Sources & evidence

ORD record
ord-acb151fcca0c40f389563bdf56a77f1c
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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