Lithium Hydroxide → 2-(3-((5-(3-Fluorophenyl)-2,3-dihydrobenzofuran-3-yl)amino)phenoxy)acetic acid

HRID 1051116Notes

Reaction equation

HRID 1051116 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH:15]([NH:18][C:19]4[CH:20]=[C:21]([CH:30]=[CH:31][CH:32]=4)[O:22][CH2:23][C:24]([O:26]C(C)C)=[O:25])[C:14]=3[CH:33]=2)[CH:7]=[CH:8][CH:9]=1>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH:15]([NH:18][C:19]4[CH:20]=[C:21]([CH:30]=[CH:31][CH:32]=4)[O:22][CH2:23][C:24]([OH:26])=[O:25])[C:14]=3[CH:33]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118161554Isopropyl 2-(3-((5-(3-fluorophenyl)-2,3-dihydrobenzofuran-3-yl)amino)phenoxy)acetate

Product 1

HCID 918104082-(3-((5-(3-Fluorophenyl)-2,3-dihydrobenzofuran-3-yl)amino)phenoxy)acetic acidYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Aqueous lithium hydroxide (1 N, 1 mL, 1 mmol) was added to a solution of isopropyl 2-(3-((5-(3-fluorophenyl)-2,3-dihydrobenzofuran-3-yl)amino)phenoxy)acetate (22 mg, 0.052 mmol) in THF (1 mL) in a scintillation vial. The vial was sealed and heated at 40° C. After 24 h, the reaction mixture was allowed to cool and the volatiles were concentrated. The residue was acidified with hydrochloric acid (1 N, 1 mL), and extracted with ethyl acetate (3×2 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford 11 mg (56%) of the title compound.

Workup

  1. customThe vial was sealed
  2. temperatureto cool
  3. concentrationthe volatiles were concentrated
  4. extractionextracted with ethyl acetate (3×2 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c6f12c3d9d4242379cbdeb61b26d1c65
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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