Sodium Hydroxide → 2-(6-(Cyclopropylmethoxy)-5-(trifluoromethyl)picolinamido)-2-ethylbutanoic acid

HRID 632310

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:14][C:15]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16]([O:18]CC)=[O:17])=[O:13])[CH:9]=[CH:8][C:7]=2[C:25]([F:28])([F:27])[F:26])[CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:14][C:15]([CH2:21][CH3:22])([CH2:23][CH3:24])[C:16]([OH:18])=[O:17])=[O:13])[CH:9]=[CH:8][C:7]=2[C:25]([F:28])([F:26])[F:27])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 2-(6-(cyclopropylmethoxy)-5-(trifluoromethyl)picolinamido)-2-ethylbutanoate (62 mg, 154 μmol) was dissolved in a mixture of 1 M aqueous sodium hydroxide solution (616 μL, 616 μmol), THF (600 μL) and MeOH (600 μL). The mixture was stirred at 60° C. for 3 d, poured onto ice water/brine/1N HCl (20 mL) and extracted with EtOAc (2×30 mL). The combined extracts were washed with ice water/brine (20 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the title compound (58 mg, quant.) as a light yellow solid. MS: 373.1 [M−H]−.

Workup

additionpoured onto ice water/brine/1N HCl (20 mL)
extractionextracted with EtOAc (2×30 mL)
washThe combined extracts were washed with ice water/brine (20 mL)
dry with materialdried over Na2SO4
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-1bcb0bc35ebe42a68237e23741bb235a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321727B2

Linked notes

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