Sodium Hydroxide → HCID 69138744, compound

HRID 1357218Notes

Reaction equation

HRID 1357218 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:16][C:17]([C:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][C:20]=3[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])[CH:12]=2)[CH:7]=1.[OH-].[Na+:34]>C1COCC1.O>[Na+:34].[CH2:28]([C:20]1[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:19]=1[C:17]([NH:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([O:5][CH2:4][C:3]([O-:32])=[O:2])[CH:15]=[CH:14]2)=[O:18])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69137592HCID 69137592, compound

Product 1

HCID 69138744HCID 69138744, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {6-[(2-butyl-benzofuran-3-carbonyl)-amino]-naphthalen-2-yloxy}-acetic acid methyl ester (103 mg, 0.239 mmol), prepared in the previous step, and 1 N NaOH (239 μL, 0.239 mmol) in 10 mL of THF plus 5 mL of water was stirred at room temperature for 21 h (overnight). The solvent was removed under reduced pressure to give the title compound (95 mg, 87%) as a yellow solid, MS m/z: 416 [M−H]−.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-553a5dcb0f1d4101ac7df222c55e69e1
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…