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Hydrochloric Acid → 2-[3-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid

HRID 1771591
Notes
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Reaction equation

HRID 1771591 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[O:20][CH2:21][C:22]([O:24]CC)=[O:23].O[Li].O.Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[O:20][CH2:21][C:22]([OH:24])=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 89443544Ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate

Product 1

HCID 715155152-[3-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate (317.0 mg, 0.83 mmol, 1.0 eq) in a mixture of THF (6 mL) and H2O (6 mL) was added LiOH.H2O (134 mg, 3.19 mmol, 4.0 eq). The reaction was stirred at room temperature for 1 h, then diluted with water (30 mL) and the solution neutralized by addition of 1M HCl. The mixture was extracted with EtOAc, the combined organic extracts were washed with brine, dried (Na2CO3), filtered and evaporated in vacuo. The residue obtained was triturated with petroleum ether and EtOAc (2:1) and the solid that formed collected by filtration, washed with petroleum ether:EtOAc (2:1) and dried to give the title compound I(a) as an off-white solid (200 mg, 68%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried (Na2CO3)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue obtained
  7. customwas triturated with petroleum ether and EtOAc (2:1)
  8. customthe solid that formed
  9. filtrationcollected by filtration
  10. washwashed with petroleum ether:EtOAc (2:1)
  11. customdried

Sources & evidence

ORD record
ord-ac54e9d846984e3ebce165de6a037350
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09249085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes