Hydrochloric Acid → (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetic acid

HRID 84827Notes

Reaction equation

HRID 84827 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([O:14]C)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[OH-].[Na+].Cl.O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67509405(R)-methyl 2-(3-bromo-4-cyanophenylamino)-2-phenylacetate

Product 1

HCID 67509737(R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetic acidYield 97.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-methyl 2-(3-bromo-4-cyanophenylamino)-2-phenylacetate (98 mg, 0.28 mmol) in THF (2 mL), 1N aq. NaOH (1.00 mL, 1.00 mmol) was added. After being stirred for 18 h, the solution was acidified with 1N HCl to pH 1-2. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo to give (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetic acid (90 mg).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc377e0db5884ad29ce46dbb5eb76bb8
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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