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

HRID 1051098Notes

Reaction equation

HRID 1051098 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[N:19]([C:23]3[CH:24]=[C:25]([CH:32]=[CH:33][CH:34]=3)[O:26][CH2:27][C:28]([O:30]C)=[O:29])[C:20](=[O:22])[CH3:21])=[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[N:19]([C:23]3[CH:24]=[C:25]([CH:32]=[CH:33][CH:34]=3)[O:26][CH2:27][C:28]([OH:30])=[O:29])[C:20](=[O:22])[CH3:21])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118161545methyl 2-(3-(N-(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)acetamido)phenoxy)acetate

Product 1

HCID 1181615442-(3-(N-(6-(3-Fluorophenyl)-2,3-dihydro-1H-inden-1-yl)acetamido)phenoxy)acetic acidYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide (1 N, 1 mL, 1 mmol) was added to a solution of methyl 2-(3-(N-(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)acetamido)phenoxy)acetate (7 mg, 0.016 mmol) in THF (1 mL) in a scintillation vial. The vial was sealed and stirred overnight at room temperature. 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 4 mg (59%) of the title compound.

Workup

  1. customThe vial was sealed
  2. waitAfter 24 h
  3. temperatureto cool
  4. concentrationthe volatiles were concentrated
  5. extractionextracted with ethyl acetate (3×2 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-01fbfd8495f74f959f95062221781afd
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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