Lithium Hydroxide → [4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-acetic acid

HRID 350995Notes

Reaction equation

HRID 350995 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([C:16]2[C:17]([O:22][C:23]3[CH:31]=[CH:30][C:26]4[O:27][CH2:28][O:29][C:25]=4[CH:24]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])=[C:8]([F:32])[CH:7]=1.[OH-].[Li+]>O1CCCC1.CO>[O:27]1[C:26]2[CH:30]=[CH:31][C:23]([O:22][C:17]3[C:16]([C:14]([NH:13][CH2:12][C:9]4[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:33])=[O:2])=[CH:7][C:8]=4[F:32])=[O:15])=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:24][C:25]=2[O:29][CH2:28]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23529350[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-acetic acid methyl ester

Product 1

HCID 9932920[4-({[2-(Benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-acetic acidYield 21%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [4-({[2-(benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-acetic acid methyl ester (0.40 g, 0.88 mmol) in tetrahydrofuran (10 mL) and methanol (2 mL) was added aqueous lithium hydroxide (2 mL, 1 M, 2 mmol). The reaction was stirred at room temperature 1 hour. The solvents were stripped in vacuo and the residue partitioned between dilute aqueous hydrochloric acid and ethyl acetate. The aqueous was extracted with 2 aliquots ethyl acetate and the pooled organics were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a yellow solid. The crude product was recrystallized from ethyl acetate to afford 80 mg of a white crystalline solid (0.18 mmol, 21% yield). mp 180° C.

Workup

  1. customthe residue partitioned between dilute aqueous hydrochloric acid and ethyl acetate
  2. extractionThe aqueous was extracted with 2 aliquots ethyl acetate
  3. washthe pooled organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow solid
  7. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c67a90f8b8343df9339c5b9106cbbdd
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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