Water → HCID 89443635, compound

HRID 1771746Notes

Reaction equation

HRID 1771746 reaction equation
[F:1][C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][CH2:7][C:8]([O:10]C(C)C)=[O:9])=[C:4]([CH3:17])[C:3]=1[NH:18][CH2:19][C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH:23]=[CH:22][C:21]=1[F:33].[Li+].[OH-].O>C1COCC1>[F:1][C:2]1[C:15]([CH3:16])=[CH:14][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([CH3:17])[C:3]=1[NH:18][CH2:19][C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=2)[CH:23]=[CH:22][C:21]=1[F:33]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 89443942Isopropyl 2-[4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,5-dimethyl-phenoxy]acetate

Product 1

HCID 89443635HCID 89443635, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl amino]-2,5-dimethyl-phenoxy]acetate (130 mg, 0.28 mmol, 1.0 eq) in THF (2 mL) was added LiOH (2M aqueous solution, 2 mL, 4 mmol, 14 eq) at room temperature. The reaction mixture was stirred at room temperature for 2 h. Water was added and THF was removed under reduced pressure. The aqueous layer was washed with MTBE and the organic extract was discarded. The aqueous layer was adjusted to pH 3-4 by addition of 3M HCl and then extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was recrystallized from CH2Cl2 (1 mL) and petroleum ether (3 mL) to give the target compound as an off-white solid (85 mg, 72%).

Workup

  1. customTHF was removed under reduced pressure
  2. washThe aqueous layer was washed with MTBE
  3. extractionthe organic extract
  4. additionThe aqueous layer was adjusted to pH 3-4 by addition of 3M HCl
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe crude product was recrystallized from CH2Cl2 (1 mL) and petroleum ether (3 mL)

Sources & evidence

ORD record
ord-1aa5bc726ed24cf48fe7caf28923f512
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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