3-Aminobenzoic Acid → 3-(((Tert-butoxy)carbonyl)amino)benzoic acid

HRID 1487102Notes

Reaction equation

HRID 1487102 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[Na+].[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O.C(OCC)(=O)C>O.O1CCOCC1>[C:17]([O:16][C:14]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])=[O:13])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 74193-Aminobenzoic AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 8541623-(((Tert-butoxy)carbonyl)amino)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 3-aminobenzoic acid (5 g, 36.5 mmol) in water (40.0 ml) was added aq. solution of sodium hydroxide (2.187 g, 54.7 mmol) followed by (BOC)2O (10.16 ml, 43.8 mmol) in dioxane (20.0 ml) under ice cooling. The mixture was stirred under ice cooling for 30 min and further at room temperature for 12 hrs. To the reaction mixture ethyl acetate (50.0 ml) was added and the aq. layer was separated. The aq. layer was acidified up to pH 4 using 2N HCl and precipitated crystals were collected by filtration (7.2 gm).

Workup

  1. customthe aq. layer was separated
  2. customprecipitated crystals
  3. filtrationwere collected by filtration (7.2 gm)

Sources & evidence

ORD record
ord-de2fa66c4ef94db795baa14b6304e4ca
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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