Lithium hydroxide, monohydrate → (3-Fluoro-phenyl)-phenylamino-acetic acid

HRID 77022Notes

Reaction equation

HRID 77022 reaction equation
C[O:2][C:3](=[O:19])[CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Li+]>C1COCC1.O>[F:18][C:14]1[CH:13]=[C:12]([CH:4]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:19])=[O:2])[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54889725Methyl 2-(3-fluorophenyl)-2-(phenylamino)acetate

Product 1

HCID 18951120(3-Fluoro-phenyl)-phenylamino-acetic acidYield 86.2%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

(3-Fluoro-phenyl)-phenylamino-acetic acid methyl ester (I97) (229 mg, 0.88 mmol) and lithium hydroxide hydrate (74.1 mg, 1.77 mmol) are dissolved in THF/water (6 mL/2 mL) and stirred at RT for 2 hours. THF is evaporated, the resulting basic aqueous solution is acidified till pH 1 with 1M HCl. The precipitate is recovered by suction filtration and washed with 1M HCl. The compound is dried at 40° C. under vacuum overnight to get intermediate I146 as a white solid (186 mg, 75% yield).

Workup

  1. customTHF is evaporated
  2. filtrationThe precipitate is recovered by suction filtration
  3. washwashed with 1M HCl
  4. customThe compound is dried at 40° C. under vacuum overnight

Sources & evidence

ORD record
ord-6787496093af47c6b6c389e7d89ea692
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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