Lithium Hydroxide → HCID 89443662, compound

HRID 1771810Notes

Reaction equation

HRID 1771810 reaction equation
[C:1]([C:3]1[C:16]([NH:17][CH2:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:22]=[CH:21][C:20]=2[F:32])=[C:15]([F:33])[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][C:7]([O:9]C(C)C)=[O:8])#[N:2].[Li+].[OH-]>C1COCC1.O>[C:1]([C:3]1[C:16]([NH:17][CH2:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[CH:22]=[CH:21][C:20]=2[F:32])=[C:15]([F:33])[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][C:7]([OH:9])=[O:8])#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89444009HCID 89444009, compound

Product 1

HCID 89443662HCID 89443662, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of isopropyl 2-[2-cyano-4-fluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate (220 mg, 0.48 mmol, 1 eq) in a mixture of THF (10 mL) and water (10 mL) was added LiOH (20 mg, 0.96 mmol, 2 eq). The reaction was stirred for 3 h then the THF removed in vacuo. The aqueous solution that remained was acidified to pH 4 with 3M HCl and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was triturated with a mixture of 2-methoxy-2-methylpropane (5 mL) and petroleum ether (20 mL) to give the desired product as an off-white solid (110 mg, 56%).

Workup

  1. customthe THF removed in vacuo
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas triturated with a mixture of 2-methoxy-2-methylpropane (5 mL) and petroleum ether (20 mL)

Sources & evidence

ORD record
ord-e5823c1733ea469f939e84e859d2eb63
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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