Hydrochloric Acid → [(4-Fluoro-phenyl)-methyl-amino]-phenyl-acetic acid hydrochloride

HRID 77001Notes

Reaction equation

HRID 77001 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH3:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.O.[OH-].[Li+].[ClH:25]>C1COCC1.O>[ClH:25].[F:20][C:17]1[CH:18]=[CH:19][C:14]([N:12]([CH:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:4]([OH:21])=[O:3])[CH3:13])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58556946Ethyl 2-((4-fluorophenyl)(methyl)amino)-2-phenylacetate

Product 1

HCID 67124664[(4-Fluoro-phenyl)-methyl-amino]-phenyl-acetic acid hydrochlorideYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(4-fluoro-phenyl)-methyl-amino]-phenyl-acetic acid ethyl ester (I70) (0.59 g, 2.05 mmol) in THF (10 mL) and water (10 mL), is added lithium hydroxide hydrate (0.26 g, 6.14 mmol). The reaction is stirred at RT for 3.5 hours and then at 70° C. for 24 hours. 3N HCl is added till pH is about 1 and the mixture is evaporated. Water (15 mL) is added and the residue is triturated obtaining a pale brown suspension that is filtered on a buckner funnel, washed with water and then with acetonitrile. The solid is dried under vacuum at 40° C. overnight to obtain intermediate I119 as a pale brown powder (0.44 g, 72% yield).

Workup

  1. waitat 70° C. for 24 hours
  2. customthe mixture is evaporated
  3. additionWater (15 mL) is added
  4. customthe residue is triturated
  5. customobtaining a pale brown suspension that
  6. filtrationis filtered on a buckner funnel
  7. washwashed with water
  8. customThe solid is dried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-033bd5ca5b0d47be8c534378e1c883d4
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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