Lithium Hydroxide → 5-(3-Chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylic acid

HRID 1036994Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

182 mg (0.50 mmol) of the compound from Example 17A are provided in 2 ml of dioxane, and 4.4 ml (8.80 mmol) of a 2N aqueous lithium hydroxide solution are added. The mixture is stirred at 50° C. for 2 hours and subsequently concentrated. The residue is diluted with water, a concentrated aqueous HCl solution is added until an acidic pH is obtained and the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 159 mg (95% of theory) of the title compound are obtained.

Workup

concentrationsubsequently concentrated
additionThe residue is diluted with water
additiona concentrated aqueous HCl solution is added until an acidic pH
customis obtained
extractionthe mixture is extracted with dichloromethane
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-b2ecb932acf143009bc64aad17843aea
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546438B2

Reaction notes

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