4-(2-Aminoethyl)benzoic acid → 4-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

HRID 515921Notes

Reaction equation

HRID 515921 reaction equation
[C:1]([O:8]C([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[NH2:12][CH2:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1>O1CCOCC1.[OH-].[Na+]>[C:4]([O:3][C:1]([NH:12][CH2:13][CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1)=[O:8])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 5060664-(2-Aminoethyl)benzoic acidHCID 22064466Tert-butyldicarbonate

Product 1

HCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl dicarbonate (1.64 g; 7.5 mmol) is dissolved in 1,4-dioxane (5 mL) and the solution is added to a well-stirred solution of 4-(2-aminoethyl)benzoic acid (1.0 g; 5 mmol) in 1M aqueous sodium hydroxide solution (25 mL) and 1,4-dioxane (10 mL), and the mixture is then stirred at ambient temperature for 3 hours. The 1,4-dioxane is removed by evaporation in vacuo, and then ethyl acetate (200 mL) is added to the residue. The pH of the aqueous phase is adjusted to 1.5 with 2M aqueous HCl solution. The organic phase is separated off and the aqueous phase is then extracted with ethyl acetate (100 mL). The combined organic extracts are washed with water, dried over Na2SO4 and evaporated to a volume of 10 mL. Heptane is added to the residue and then the solid precipitate is filtered off to yield the title compound.

Workup

  1. customThe 1,4-dioxane is removed by evaporation in vacuo
  2. additionethyl acetate (200 mL) is added to the residue
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is then extracted with ethyl acetate (100 mL)
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated to a volume of 10 mL
  8. additionHeptane is added to the residue
  9. filtrationthe solid precipitate is filtered off

Sources & evidence

ORD record
ord-936255d934364548afffe4f4747b54e7
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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