Ethyl Acetate → Methyl 2-(2-benzyloxy-6-fluoroanilino)-acetate

HRID 889271Notes

Reaction equation

HRID 889271 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:10]=1[NH:11][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 15219197HCID 15219197, compound

Product 1

HCID 68430918Methyl 2-(2-benzyloxy-6-fluoroanilino)-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-benzyloxy-6-fluoroaniline (950 mg, 4.37 mmol), methyl bromoacetate (456 μL, 737 mg, 4.82 mmol), and potassium carbonate (1.21 g, 8.76 mmols) in DMF (10 mL) is heated at 60° C. for 18 h. The mixture is poured into ethyl acetate and extracted once with water and five times with brine. The organic layer is dried, filtered, and the solvent removed under reduced pressure to afford a crude oil that is chromatographed on an Isco Companion (80 g silica gel, 0-30% gradient of hexane/ethyl acetate) to afford methyl 2-(2-benzyloxy-6-fluoroanilino)-acetate as an oil. MS (M+1)+=290; NMR (CDCl3): δ 7.39 (m, 5H), 6.67 (m, 3H), 5.10 (s, 2H), 4.57 (br s, 1H), 4.11 (m, 2H), 3.72 (s, 3H).

Workup

  1. extractionextracted once with water and five times with brine
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customto afford a crude oil that
  6. customis chromatographed on an Isco Companion (80 g silica gel, 0-30% gradient of hexane/ethyl acetate)

Sources & evidence

ORD record
ord-84bc523a57de4e5baf62d1c7e360d8fe
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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