Hydrochloric Acid → 5-(Ethyl-isobutyryl-amino)-4'-methyl-biphenyl-3-carboxylic acid

HRID 2061723Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:8]=[C:9]([N:11]([CH2:17][CH3:18])[C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[CH:10]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1.O>[CH2:17]([N:11]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[CH:8]=1)[CH3:18]

Participants

Conditions

Temperature: 50 °C

Procedure

5-(Ethyl-isobutyryl-amino)-4′-methyl-biphenyl-3-carboxylic acid methyl ester (0.461 g, 1.36 mmol) was dissolved in THF (10 mL). To this THF solution was added a solution of LiOH (0.342 g) in water (8 mL). The mixture was stirred at 50° C. for three hours, then cooled to room temperature. The mixture was acidified by addition of 1N aqueous HCl and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 0.46 g of 5-(ethyl-isobutyryl-amino)-4′-methyl-biphenyl-3-carboxylic acid as a clear foam.

Workup

temperaturecooled to room temperature
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-dc993da7f6ce45d9864d251161d0cf07
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283383B2

Reaction notes

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