1-(5-Amino-2-fluorophenyl)ethanone → tert-butyl N-(3-acetyl-4-fluorophenyl)carbamate

HRID 48346Notes

Reaction equation

HRID 48346 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C:12](OC([O-])=O)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>O1CCCC1>[C:15]([O:14][C:12](=[O:13])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 27811251-(5-Amino-2-fluorophenyl)ethanoneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 69892153tert-butyl N-(3-acetyl-4-fluorophenyl)carbamateYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.19 g (7.77 mmol) of 1-(5-amino-2-fluorophenyl)ethanone in 18 ml of dry tetrahydrofuran at room temperature under an atmosphere of nitrogen was added 1.86 g (8.54 mol) of tert-butyl dicarbonate. The solution was stirred for 28 hours at room temperature followed by 17 hours at 45° C., cooled to room temperature and evaporated under reduced pressure. The residue was dissolved in ethyl acetate and the solution washed with sodium bicarbonate solution, dried over magnesium sulphate, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate/petrol 4:1 for the elution. There was obtained 1.45 g of (3-acetyl-4-fluorophenyl)carbamic acid tert-butyl ester MS: m/e 271 [M+CH3CN]+.

Workup

  1. waitfollowed by 17 hours at 45° C.
  2. temperaturecooled to room temperature
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution washed with sodium bicarbonate solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness
  8. customthe residue chromatographed on silica gel
  9. washfor the elution

Sources & evidence

ORD record
ord-eb4b1ec7feed439285bc1d43c0f88051
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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