Lithium Hydroxide → 2-(3-((6-(3-Fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetic acid

HRID 1051095Notes

Reaction equation

HRID 1051095 reaction equation
[OH-].[Li+].[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH:16]3[NH:19][C:20]3[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=3)[O:23][CH2:24][C:25]([O:27]C(C)C)=[O:26])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH2:14][CH2:15][CH:16]3[NH:19][C:20]3[CH:21]=[C:22]([CH:31]=[CH:32][CH:33]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118161547isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate

Product 1

HCID 1181615432-(3-((6-(3-Fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetic acidYield 76%

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-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate (25 mg, 0.06 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 17 mg (76%) 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-7e1f186a5660415d8463c713a8d93120
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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