Sodium Hydroxide → 6-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthoic acid sodium salt

HRID 1693646Notes

Reaction equation

HRID 1693646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:32]([OH:34])=[O:33])=[CH:27][CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:35]([CH3:37])[CH3:36])[O:11][N:10]=1.[OH-].[Na+:39]>CO>[Na+:39].[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[C:28]([C:32]([O-:34])=[O:33])=[CH:27][CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:35]([CH3:37])[CH3:36])[O:11][N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16214849Gsk-8062

Product 1

HCID 237008436-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthoic acid sodium salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mechanically stirred suspension of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylic acid (166 g, 0.31 mol) in methanol (500 mL) was treated with 1N sodium hydroxide (327 mL). The resulting solution was stirred at room temperature. The mixture was stirred 1 h and the resulting solid was collected by filtration, washed with acetone, hexane and then dried to give 151 g of the product as a white solid. 1H NMR (DMSO-d6): 9.04 (d, J=9 Hz, 1H), 8.00 (s, 1H), 7.78 (d, J=8 Hz, 1H), 7.72 (d, J=7 Hz, 1H), 7.66-7.61 (m, 5H), 7.53 (dd, J=7, 9 Hz, 1H), 7.37 (t, J=8 Hz, 1H), 6.88 (d, J=9 Hz, 2H), 4.85 (s, 2H), 3.46 (septet, J=7 Hz, 1H), 1.32 (d, J=7 Hz, 6H). ESI-LCMS m/z 532 (M+H)+.

Workup

  1. stirringThe mixture was stirred 1 h
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with acetone, hexane
  4. customdried

Sources & evidence

ORD record
ord-66ad23a9d6ea43088cfe77984f5fc8a4
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

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