Hydrochloric Acid → 2'-Cyano-4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid

HRID 1845282Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[C:12]([C:22]([O:24]C)=[O:23])[CH:11]=1)#[N:2].[OH-].[Li+].Cl>O1CCCC1>[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:4]=1[C:10]1[CH:15]=[C:14]([O:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[C:12]([C:22]([OH:24])=[O:23])[CH:11]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2′-cyano-4′-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate (112 mg, 0.32 mmol) in tetrahydrofuran (2 mL) was added 2.5 M of aqueous lithium hydroxide solution (0.72 mL, 1.8 mmol). The reaction mixture was stirred at 60° C. overnight. The aqueous solution was acidified with 15% HCl (aq.) to pH=5, and extracted with EtOAc. The combined organic layers were concentrated in vacuo to get the title compound as a white solid.

Workup

extractionextracted with EtOAc
concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record: ord-b512cb44d720452e9eb6b49b4687e905
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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