Water → HCID 67304775, compound

HRID 1009471Notes

Reaction equation

HRID 1009471 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:2]([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].CC(C)([O-])C.[K+].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][C:34]=1[F:35])[C:27]([O:29]CC)=[O:28].O>CN(C=O)C>[C:12]([O:11][C:9]([N:1]([CH2:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][C:34]=1[F:35])[C:27]([OH:29])=[O:28])[C:2]([O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[O:3])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 279800Di-tert-butyl IminodicarboxylateHCID 23665647Potassium tert-butoxideHCID 58009419HCID 58009419, compound

Product 1

HCID 67304775HCID 67304775, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.56 g of di-tert-butyl iminodicarboxylate was dissolved in 20.0 mL of DMF, and 804 mg of potassium tert-butoxide was added under ice-cooling, followed by stirring at room temperature for 1 hour. To the reaction liquid was added dropwise a solution (10.0 mL) of 1.70 g of ethyl 3-(bromomethyl)-4-fluorobenzoate in DMF, followed by stirring at room temperature overnight. The reaction liquid was poured to water, followed by extraction with ethyl acetate, and the organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 2.59 g of 3-{[bis(tert-butoxycarbonyl)amino]methyl}-4-fluorobenzoic acid.

Workup

  1. temperaturecooling
  2. customTo the reaction liquid
  3. stirringby stirring at room temperature overnight
  4. customThe reaction liquid
  5. extractionfollowed by extraction with ethyl acetate
  6. washthe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21c4e92b031049aca8b6371d7b21b12d
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

Loading…