Acetic Acid → HCID 57411216, compound

HRID 623907Notes

Reaction equation

HRID 623907 reaction equation
[CH:1]1([CH2:4][C:5]2[NH:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([CH3:31])=[CH:18][C:19]([O:22][CH2:23][C:24]([CH3:30])([CH3:29])[C:25]([O:27]C)=[O:26])=[N:20][CH:21]=4)=[CH:12][C:11]=3[F:32])=[N:7][CH:6]=2)[CH2:3][CH2:2]1.[OH-].[Na+].O.C(O)(=O)C>O1CCCC1.CO>[CH:1]1([CH2:4][C:5]2[NH:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([CH3:31])=[CH:18][C:19]([O:22][CH2:23][C:24]([CH3:29])([CH3:30])[C:25]([OH:27])=[O:26])=[N:20][CH:21]=4)=[CH:12][C:11]=3[F:32])=[N:7][CH:6]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67975334HCID 67975334, compound

Product 1

HCID 57411216HCID 57411216, compoundYield 141.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In tetrahydrofuran (10 mL) and methanol (10 mL) was dissolved methyl 3-[(5-{4-[5-(cyclopropylmethyl)-1H-imidazol-2-yl]-3-fluorophenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoate (247 mg), and after adding 2N aqueous sodium hydroxide solution (2.8 mL) to the solution, the resulting mixture was stirred at 50° C. for 7 hours. Water and acetic acid were added to the residue obtained by concentrating the reaction mixture under reduced pressure. The precipitated solid was collected by filtration, washed with water and dried to obtain 3-[(5-{4-[5-(cyclopropylmethyl)-1H-imidazol-2-yl]-3-fluorophenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoic acid (339 mg).

Workup

  1. customobtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-eb8ec26f993e4127b0a2fc34aec63d95
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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