4-Fluoroaniline → (R)-(4-fluoro-phenylamino)-phenyl-acetic acid methyl ester

HRID 77051Notes

Reaction equation

HRID 77051 reaction equation
CS(O[C@@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8])(=O)=O.[F:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>CC#N>[CH3:10][O:9][C:7](=[O:8])[C@H:6]([NH:22][C:21]1[CH:23]=[CH:24][C:18]([F:17])=[CH:19][CH:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 10999262(S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate

Product 1

HCID 59401123(R)-(4-fluoro-phenylamino)-phenyl-acetic acid methyl esterYield 94.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (S)-methyl 2-(methylsulfonyloxy)-2-phenylacetate (I5) (520 mg, 2.13 mmol) in CH3CN (10 mL), is added 4-fluoroaniline (473 mg, 4.26 mmol) and the mixture is heated at 120° C. for 5 minutes under MW irradiation (UPLC-MS: complete conversion). Acetonitrile was evaporated and the resulting crude is dissolved in 1N HCl and extracted several times with EtOAc. The combined organic phase is dried over Na2SO4, filtered and evaporated to dryness to obtain intermediate I254 as a pale yellow oil (520 mg, 94% yield).

Workup

  1. customAcetonitrile was evaporated
  2. dissolutionthe resulting crude is dissolved in 1N HCl
  3. extractionextracted several times with EtOAc
  4. dry with materialThe combined organic phase is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5d4cd55e8bcb4eba81382997411fbf1a
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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