4-Aminosalicylic Acid → 4-(((Tert-butoxy)carbonyl)amino)-2-hydroxybenzoic acid

HRID 1595193Notes

Reaction equation

HRID 1595193 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[OH-].[Na+].C(OC(O)=O)(O)=O.[C:21](=O)([O:27]C(C)(C)C)[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>O1CCOCC1.O>[C:23]([O:22][C:21]([NH:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7])=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 46494-Aminosalicylic AcidHCID 14798Sodium HydroxideHCID 86757352HCID 86757352, compound

Product 1

HCID 103324764-(((Tert-butoxy)carbonyl)amino)-2-hydroxybenzoic acidYield 55.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

4-Aminosalicylic acid (5.00 g, 32.6 mmol) was suspended in dioxane (35 ml) and water (35 ml), and the suspension was added with aqueous sodium hydroxide (2N) and a solution of di-tert-butyl carbonate dicarbonate (8.5 g, 39.0 mmol) in dioxane (35 ml), and then the mixture was stirred at room temperature for seven days. After the dioxane of the reaction mixture was evaporated, the residue was made weakly acidic (pH˜4) with 1N hydrochloric acid, and then extracted with ether. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated. The resulting syrup was solidified with hexane and ethyl acetate to obtain the title compound (4.58 g, yield; 55%).

Workup

  1. customAfter the dioxane of the reaction mixture was evaporated
  2. extractionextracted with ether
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d2858681d8c14745af2b19351282c4d3
Source dataset
uspto-grants-2001_09
Patent number
US06288041B1

Reaction notes

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