Sodium Hydroxide → HCID 67299617, compound

HRID 1881035Notes

Reaction equation

HRID 1881035 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][C:17]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:9][CH:8]=1.[OH-].[Na+]>CO.O1CCCC1>[C:23]1([C:18]2[C:17]([NH:16][CH2:15][CH2:14][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:12][CH:11]=3)=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67299427HCID 67299427, compound

Product 1

HCID 67299617HCID 67299617, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-{4-[2-(2-phenylpyridinylamino)ethoxy]phenyl}butanoic acid methyl ester (149 mg) from the previous step was dissolved in methanol (2 mL) and tetrahydrofuran (2 mL), and 2N sodium hydroxide aqueous solution (0.6 mL) was added, then stirred overnight at room temperature. The reaction solution was concentrated with 2N hydrochloric acid (0.6 mL), then the residue was purified by silica gel flash column chromatography (developing solvent: chloroform:methanol=19:1) to give the above-identified compound (115 mg, yield 80%) as a colorless crystal.

Workup

  1. concentrationThe reaction solution was concentrated with 2N hydrochloric acid (0.6 mL)
  2. customthe residue was purified by silica gel flash column chromatography (developing solvent: chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-e3f4a3dd12f34afbb1a11e12baa75fab
Source dataset
uspto-grants-2012_11
Patent number
US08318781B2

Reaction notes

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