Hydrochloric Acid → 2-(4-Chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenoxy)butanoic acid

HRID 2390376Notes

Reaction equation

[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]([CH2:13][CH3:14])[C:8]([O:10]CC)=[O:9])=[C:4]([C:17]#[C:18][C:19]2[CH:24]=[C:23]([S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=2[CH3:31])[CH:3]=1.[OH-].[Na+].Cl>CCO.O>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]([CH2:13][CH3:14])[C:8]([OH:10])=[O:9])=[C:4]([C:17]#[C:18][C:19]2[CH:24]=[C:23]([S:25]([CH2:28][CH2:29][CH3:30])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=2[CH3:31])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of ethyl 2-(4-chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenoxy)butanoate (Intermediate 268; 100 mg; 0.11 mmol) in EtOH (1 ml) was treated with a 1M solution of sodium hydroxide in water (0.16 ml; 0.16 mmol). After stirring at 70° C. for 45 minutes, a 1 N solution of HCl in water (65 μl) was added, the solvents removed under reduced pressure and the residue purified by preparative HPLC to afford the title compound as a beige solid.

Workup

customthe solvents removed under reduced pressure
customthe residue purified by preparative HPLC

Sources & evidence

ORD record: ord-5ad8e66697e84f8996fe1d4f2ea1d725
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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