Sodium Hydroxide → HCID 10203111, compound

HRID 1836868Notes

Reaction equation

HRID 1836868 reaction equation
[F:1][C:2]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]2[C:23]([CH2:24][N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)=[CH:22][C:21]3[C:20]([CH3:31])([CH3:30])[CH2:19][CH2:18][C:17]([CH3:33])([CH3:32])[C:16]=3[CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[F:1][C:2]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]2[C:23]([CH2:24][N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)=[CH:22][C:21]3[C:20]([CH3:31])([CH3:30])[CH2:19][CH2:18][C:17]([CH3:33])([CH3:32])[C:16]=3[CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 69156357HCID 69156357, compound

Product 1

HCID 10203111HCID 10203111, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of 199 mg (0.446 mmol) of Methyl 2-fluoro-4-[(E)-2-[5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate, 1.5 mL ethanol and 1 mL of 2M aqueous sodium hydroxide was stirred for 16 hours. The mixture was neutralized with aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was then washed with brine, dried over magnesium sulfate and concentrated in vacuo. The resulting 145 mg of residue was triturated in methanol to provide 85 mg (44%) of 2-Fluoro-4-[(E)-2-[5,5,8,8-tetramethyl-3-pyrazol-1-ylmethyl-5,6,7,8-tetrahydro naphthalen-2-yl)vinyl]benzoic acid 47.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting 145 mg of residue was triturated in methanol

Sources & evidence

ORD record
ord-a30b4ceeee9048dab38d9ceecb58cb5c
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

Loading…