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

HRID 340623Notes

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-a56bd502f7fa41b0997855f3864c06ef
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895589B2

Reaction notes

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