Hydrochloric Acid → 2-(3-Fluorophenyl)-2-(3-fluorophenylamino)acetic acid

HRID 76969Notes

Reaction equation

HRID 76969 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:9]([O:11]CC)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59401185HCID 59401185, compound

Product 1

HCID 548906902-(3-Fluorophenyl)-2-(3-fluorophenylamino)acetic acidYield 99%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of ethyl 2-(3-fluorophenyl)-2-(3-fluorophenylamino)-acetate (2.00 g, 6.81 mmol) in THF/H2O (1:1 mixture, 10 mL), is added LiOH (816 mg, 34.0 mmol) and the mixture is reacted for 2 hours at RT (LC-MS monitoring: complete conversion). 1N HCl (15 mL) is added and the desired compound is extracted with EtOAc. The resulting crude is purified by flash chromatography (Hexane/EtOAc=1/1) in order to obtain 1.79 g of I11 as a pale yellow solid (99% yield).

Workup

  1. customthe mixture is reacted for 2 hours at RT (LC-MS monitoring: complete conversion)
  2. extractionthe desired compound is extracted with EtOAc
  3. customThe resulting crude is purified by flash chromatography (Hexane/EtOAc=1/1) in order

Sources & evidence

ORD record
ord-8af632b6c3014e1e83b01aaffa61830d
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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